2-(Dimethylamino)acetyl chloride → HCID 25254779, compound
Reaction equation
[CH:1]1([N:7]2[CH2:13][C:12]([F:15])([F:14])[C:11](=[O:16])[N:10]([CH3:17])[C:9]3[CH:18]=[N:19][C:20]([NH:22][C:23]4[CH:37]=[CH:36][C:26]([C:27]([NH:29][CH:30]5[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]5)=[O:28])=[CH:25][C:24]=4[O:38][CH3:39])=[N:21][C:8]2=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:40][N:41]([CH3:46])[CH2:42][C:43](Cl)=[O:44]>>[CH:1]1([N:7]2[CH2:13][C:12]([F:15])([F:14])[C:11](=[O:16])[N:10]([CH3:17])[C:9]3[CH:18]=[N:19][C:20]([NH:22][C:23]4[CH:37]=[CH:36][C:26]([C:27]([NH:29][CH:30]5[CH2:35][CH2:34][N:33]([C:43](=[O:44])[CH2:42][N:41]([CH3:46])[CH3:40])[CH2:32][CH2:31]5)=[O:28])=[CH:25][C:24]=4[O:38][CH3:39])=[N:21][C:8]2=3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1Participants
Procedure
The title compound was synthesized from 4-(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-N-(piperidin-4-yl)benzamide and 2-(dimethylamino)acetyl chloride. The final compound was purified by reverse phase HPLC and basified to give the free base. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.14-1.25 (m, 1 H) 1.33-1.46 (m, 3 H) 1.48-1.65 (m, 3 H) 1.72-1.90 (m, 6 H) 2.35 (s, 6 H) 2.72 (t, J=12.2 Hz, 1 H) 2.72 (t, 1 H) 3.10 (t, J=11.8 Hz, 1 H) 3.31 (s, 3 H) 3.47 (d, 1 H) 3.94 (s, 3 H) 4.06 (t, J=13.5 Hz, 2 H) 3.97-4.12 (m, 2 H) 4.35 (d, 1 H) 4.46 (br. s., 1 H) 7.47 (dd, J=8.4, 1.6 Hz, 1 H) 7.50 (d, J=1.7 Hz, 1 H) 7.91 (s, 1 H) 8.19 (d, J=8.1 Hz, 1 H) 8.21 (s, 1 H) 8.27 (d, J=8.3 Hz, 1 H). Melting point: 190-191° C. [M+H] calc'd for C31H42F2N8O4 629; found 629.
Workup
- customThe final compound was purified by reverse phase HPLC
- customto give the free base
Sources & evidence
- ORD record
- ord-0066284dee6347869c1ab318f173e3aa
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318727B2
Reaction notes
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