N,N-Dimethylglycine → HCID 25255103, compound

HRID 1880905Notes

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][N: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](O)=[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][N: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]1

Participants

Reactant 2

HCID 673N,N-Dimethylglycine

HCID 25254940HCID 25254940, compound

Product 1

HCID 25255103HCID 25255103, compound

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-(piperazin-1-yl)benzamide using a procedure that is analogous to that described in connection with amide formation except that N,N-dimethylglycine. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.12-1.89 (m, 10 H) 2.19 (s, 6 H) 2.89 (br. s., 2 H) 2.94 (br. s., 2 H) 3.31 (s, 3 H) 3.54 (br. s., 2 H) 3.63 (br. s., 2 H) 3.93 (s, 3 H) 4.06 (t, J=13.39 Hz, 2 H) 4.46 (m, 1 H) 7.42 (d, J=8.0 Hz, 1 H) 7.44 (s, 1 H) 7.91 (s, 1 H) 8.21 (s, 1 H) 8.28 (d, J=8.33 Hz, 1 H) 9.52 (s, 1 H). [M+H] calculated for C30H41F2N9O4, 630; found 630.

Sources & evidence

ORD record: ord-484811147b234852b8ee57a60d7fb4f9
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318727B2

Reaction notes

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