3-Fluoro-4-(4-methylpiperazin-1-yl)aniline → HCID 57955647, compound

HRID 1881001Notes

Reaction equation

HRID 1881001 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.[F:33][C:34]1[CH:35]=[C:36]([CH:38]=[CH:39][C:40]=1[N:41]1[CH2:46][CH2:45][N:44]([CH3:47])[CH2:43][CH2:42]1)[NH2:37]>>[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:37][C:36]5[CH:38]=[CH:39][C:40]([N:41]6[CH2:46][CH2:45][N:44]([CH3:47])[CH2:43][CH2:42]6)=[C:34]([F:33])[CH:35]=5)=[O:27])=[CH:24][C:23]=4[O:31][CH3:32])=[N:20][C:7]2=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 27830553-Fluoro-4-(4-methylpiperazin-1-yl)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 57955647HCID 57955647, compound

Procedure

The title compound was prepared in a manner analogous to the 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 3-fluoro-4-(4-methylpiperazin-1-yl)aniline with yield 52.4 mg (41%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.60 (br. s., 6 H) 1.99 (s, 2 H) 2.22 (s, 3 H) 2.40-2.51 (m, 4 H) 2.98 (br. s., 4 H) 3.97 (s, 3 H) 4.22 (t, 2 H) 4.79 (m, 1 H) 7.03 (t, J=9.35 Hz, 1 H) 7.45 (dd, J=8.72, 1.64 Hz, 1 H) 7.54-7.78 (m, 3 H) 8.04 (s, 1 H) 8.28 (s, 1 H) 8.36 (d, J=8.34 Hz, 1 H) 10.11 (s, 1 H). [M+H] calc'd for C32H37F2N8O3, 639; found 639.

Sources & evidence

ORD record
ord-f0db049904d74f45aef8dc87edd17e4e
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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