3-(4-Methylpiperazin-1-yl)aniline → HCID 57955568, compound

HRID 914232Notes

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]([OH:28])=O)=[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:41]=[C:42]([CH:44]=[CH:45][CH:46]=2)[NH2:43])[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:43][C:42]5[CH:44]=[CH:45][CH:46]=[C:40]([N:37]6[CH2:36][CH2:35][N:34]([CH3:33])[CH2:39][CH2:38]6)[CH:41]=5)=[O:28])=[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

Reactant 2

HCID 115646133-(4-Methylpiperazin-1-yl)aniline

HCID 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 57955568HCID 57955568, 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 3-(4-methylpiperazin-1-yl)aniline with yield 35 mg (28%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.43-1.72 (m, 6H) 1.98 (br. s., 2H) 2.22 (s, 2H) 2.35-2.50 (m, 4H) 2.97-3.23 (m, 4H) 3.98 (s, 3H) 4.06 (t, J=12 Hz, 2H) 4.79 (m, 1H) 6.55-6.79 (m, 1H) 7.12-7.26 (m, 2H) 7.40 (s, 1H) 7.52-7.72 (m, 2H) 8.03 (s, 1H) 8.28 (s, 1H) 8.35 (d, J=8.34 Hz, 1H) 9.94 (s, 1H). [M+H] calc'd for C32H38F2N8O3, 621. found 621.

Sources & evidence

ORD record: ord-6a9055a8ca654447ac2abf02030a3a18
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026234B2

Reaction notes

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