4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-2-fluoro-5-methoxybenzoic acid → 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[5,4-b][1,4]diazepin-2-ylamino)-2-fluoro-5-methoxy-N-(3-((4-methylpiperazin-1-yl)methyl)phenyl)benzamide

HRID 1881005Notes

Reaction equation

HRID 1881005 reaction equation
[CH:1]1([N:6]2[CH2:12][C:11]([F:14])([F:13])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[C:30]([O:31][CH3:32])=[CH:29][C:25]([C:26](O)=[O:27])=[C:24]([F:33])[CH:23]=4)=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[CH3:35][N:36]1[CH2:41][CH2:40][N:39]([CH2:42][C:43]2[CH:44]=[C:45]([CH:47]=[CH:48][CH:49]=2)[NH2:46])[CH2:38][CH2:37]1>>[CH:1]1([N:6]2[CH2:12][C:11]([F:13])([F:14])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[C:30]([O:31][CH3:32])=[CH:29][C:25]([C:26]([NH:46][C:45]5[CH:47]=[CH:48][CH:49]=[C:43]([CH2:42][N:39]6[CH2:38][CH2:37][N:36]([CH3:35])[CH2:41][CH2:40]6)[CH:44]=5)=[O:27])=[C:24]([F:33])[CH:23]=4)=[N:20][C:7]2=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 252536794-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-2-fluoro-5-methoxybenzoic acidHCID 67117813HCID 67117813, compound

Product 1

HCID 579556024-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[5,4-b][1,4]diazepin-2-ylamino)-2-fluoro-5-methoxy-N-(3-((4-methylpiperazin-1-yl)methyl)phenyl)benzamide

Procedure

The title compound was prepared in a manner analogous to compound 149 from 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[5,4-b][1,4]diazepin-2-ylamino)-2-fluoro-5-methoxybenzoic acid and 3-((4-methylpiperazin-1-yl)methyl)aniline hydrochloride with yield 43 mg (33%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.62 (br. s., 6 H) 1.99 (br. s., 2 H) 2.14 (s, 3 H) 2.33 (br. s., 8 H) 3.43 (s, 2 H) 3.94 (s, 3 H) 4.09 (t, J=13.89 Hz, 2 H) 4.84 (br. s., 1 H) 7.01 (d, J=7.58 Hz, 1 H) 7.20-7.35 (m, 2 H) 7.61 (br. s., 1 H) 7.67 (br. s., 1 H) 8.10 (s, 1 H) 8.23-8.40 (m, 2 H) 10.14 (s, 1 H). [M+H] calc'd for C33H39F3N8O3, 653; found 653.

Sources & evidence

ORD record
ord-505427af8f3041b7ba9fde90c3fcc9c3
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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