[NH2:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[NH:7][C:8]1[N:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:18]3[CH:29]=[CH:28][C:21]([C:22]([NH:24][CH:25]4[CH2:27][CH2:26]4)=[O:23])=[CH:20][C:19]=3[O:30][CH3:31])[CH:14]=2)[N:9]=1.[C:32](O)(=[O:35])[C:33]#[CH:34].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>ClCCl>[CH:25]1([NH:24][C:22](=[O:23])[C:21]2[CH:28]=[CH:29][C:18]([C:13]3[CH:14]=[C:15]4[C:10](=[CH:11][CH:12]=3)[N:9]=[C:8]([NH:7][C@@H:3]3[CH2:4][CH2:5][CH2:6][C@@H:2]3[NH:1][C:32](=[O:35])[C:33]#[CH:34])[N:17]=[CH:16]4)=[C:19]([O:30][CH3:31])[CH:20]=2)[CH2:27][CH2:26]1A mixture of 4-(2-(((1R,2S)-2-aminocyclopentyl)amino)quinazolin-6-yl)-N-cyclopropyl-3-methoxybenzamide (0.11 mmol), propiolic acid (0.010 mL, 0.17 mmol), HATU (64 mg, 0.17 mmol) and DIEA (0.06 mL, 0.34 mmol) in dichloromethane (1.5 mL) was stirred at room temperature for 45 minutes. LC-MS indicated complete consumption of SM. The reaction mixture was purified by silica gel chromatography to yield N-cyclopropyl-3-methoxy-4-(2-(((1R,2S)-2-propiolamidocyclopentyl)amino)quinazolin-6-yl)benzamide (Compound 13) (35 mg, 69%). MS (ES+) C27H27N5O3 requires: 469, found: 470 [M+H]+.
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