Evaluation of Kilogram-Scale Sonagashira, Suzuki, and Heck Coupling Routes to Oncology Candidate CP-724,714
The synthesis of the anti-cancer compound 2-methoxy-N-(3-{4-[3-methyl-4-(6-methyl-pyridin-3-yloxy)phenylamino]quinazolin-6-yl}-E-allyl)acetamide (CP-724,714) (1) on multikilogram scale using several different synthetic routes is described. Application of the Sonogashira, Suzuki, and Heck couplings t...
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| Veröffentlicht in: | Organic process research & development 2005-07, Vol.9 (4), p.440-450 |
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| creator | Ripin, David H. Brown Bourassa, Dennis E Brandt, Thomas Castaldi, Michael J Frost, Heather N Hawkins, Joel Johnson, Phillip J Massett, Stephen S Neumann, Karin Phillips, James Raggon, Jeffery W Rose, Peter R Rutherford, Jennifer L Sitter, Barbara Stewart, A. Morgan Vetelino, Michael G Wei, Lulin |
| description | The synthesis of the anti-cancer compound 2-methoxy-N-(3-{4-[3-methyl-4-(6-methyl-pyridin-3-yloxy)phenylamino]quinazolin-6-yl}-E-allyl)acetamide (CP-724,714) (1) on multikilogram scale using several different synthetic routes is described. Application of the Sonogashira, Suzuki, and Heck couplings to this synthesis was investigated to identify a safe, environmentally friendly, and robust process for the production of this drug candidate. A convergent and selective synthesis of the candidate was identified which utilizes a Heck coupling of a protected allylamine to install the critical olefin. |
| doi_str_mv | 10.1021/op050039u |
| format | Article |
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Brown ; Bourassa, Dennis E ; Brandt, Thomas ; Castaldi, Michael J ; Frost, Heather N ; Hawkins, Joel ; Johnson, Phillip J ; Massett, Stephen S ; Neumann, Karin ; Phillips, James ; Raggon, Jeffery W ; Rose, Peter R ; Rutherford, Jennifer L ; Sitter, Barbara ; Stewart, A. Morgan ; Vetelino, Michael G ; Wei, Lulin</creator><creatorcontrib>Ripin, David H. Brown ; Bourassa, Dennis E ; Brandt, Thomas ; Castaldi, Michael J ; Frost, Heather N ; Hawkins, Joel ; Johnson, Phillip J ; Massett, Stephen S ; Neumann, Karin ; Phillips, James ; Raggon, Jeffery W ; Rose, Peter R ; Rutherford, Jennifer L ; Sitter, Barbara ; Stewart, A. Morgan ; Vetelino, Michael G ; Wei, Lulin</creatorcontrib><description>The synthesis of the anti-cancer compound 2-methoxy-N-(3-{4-[3-methyl-4-(6-methyl-pyridin-3-yloxy)phenylamino]quinazolin-6-yl}-E-allyl)acetamide (CP-724,714) (1) on multikilogram scale using several different synthetic routes is described. Application of the Sonogashira, Suzuki, and Heck couplings to this synthesis was investigated to identify a safe, environmentally friendly, and robust process for the production of this drug candidate. 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| title | Evaluation of Kilogram-Scale Sonagashira, Suzuki, and Heck Coupling Routes to Oncology Candidate CP-724,714 |
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