4-(4-methylpiperazin-1-yl)-3-(trifluoromethyl)aniline → HCID 57955643, compound

HRID 1881002Notes

Reaction equation

HRID 1881002 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[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][C:23]=4[O:31][CH3:32])=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:33][N:34]1[CH2:39][CH2:38][N:37]([C:40]2[CH:46]=[CH:45][C:43]([NH2:44])=[CH:42][C:41]=2[C:47]([F:50])([F:49])[F:48])[CH2:36][CH2:35]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[CH:30]=[CH:29][C:25]([C:26]([NH:44][C:43]5[CH:45]=[CH:46][C:40]([N:37]6[CH2:38][CH2:39][N:34]([CH3:33])[CH2:35][CH2:36]6)=[C:41]([C:47]([F:50])([F:49])[F:48])[CH:42]=5)=[O:27])=[CH:24][C:23]=4[O:31][CH3:32])=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 65004004-(4-methylpiperazin-1-yl)-3-(trifluoromethyl)anilineHCID 252529054-(9-Cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[5,4-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid

Product 1

HCID 57955643HCID 57955643, compound

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)-3-methoxybenzoic acid and 4-(4-methylpiperazin-1-yl)-3-(trifluoromethyl)aniline with yield 46 mg (34%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.43-1.72 (m, 6 H) 1.99 (br. s., 2 H) 2.23 (s, 3 H) 2.47 (br.s., 4 H) 2.85 (t, J=4.29 Hz, 4 H) 3.99 (s, 3 H) 4.07 (t, J=12 Hz, 2 H) 4.80 (t, J=7.96 Hz, 1 H) 7.46-7.73 (m, 3 H) 7.97-8.10 (m, 2 H) 8.14 (d, J=2.53 Hz, 1 H) 8.29 (s, 1 H) 8.38 (d, J=8.34 Hz, 1 H) 10.31 (s, 1 H). [M+H] calc'd for C33H37F5N8O3, 689; found 689.

Sources & evidence

ORD record
ord-4bbbdae9491f470d967124e6b58d93d7
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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