Benzamide, N-cyclopropyl-4-(1-piperazinyl)- → HCID 66716888, compound

HRID 1184478Notes

Reaction equation

HRID 1184478 reaction equation
[CH:1]1([C:4]2[C:9]3[O:10][CH:11]([CH3:15])[C:12](=[O:14])[NH:13][C:8]=3[CH:7]=[C:6]([CH:16]=O)[CH:5]=2)[CH2:3][CH2:2]1.[CH:18]1([NH:21][C:22](=[O:35])[C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)=[CH:25][CH:24]=2)[CH2:20][CH2:19]1>>[CH:18]1([NH:21][C:22](=[O:35])[C:23]2[CH:24]=[CH:25][C:26]([N:29]3[CH2:30][CH2:31][N:32]([CH2:16][C:6]4[CH:5]=[C:4]([CH:1]5[CH2:2][CH2:3]5)[C:9]5[O:10][CH:11]([CH3:15])[C:12](=[O:14])[NH:13][C:8]=5[CH:7]=4)[CH2:33][CH2:34]3)=[CH:27][CH:28]=2)[CH2:20][CH2:19]1

Participants

3

Reactant 2

HCID 28749052Benzamide, N-cyclopropyl-4-(1-piperazinyl)-HCID 86664220HCID 86664220, compound

Product 1

HCID 66716888HCID 66716888, compound

Procedure

Using 346A and N-cyclopropyl-4-(piperazin-1-yl)benzamide 284 in the general procedure for reductive aminations, the title compound was obtained as an off-white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 0.50-0.57 (m, 2H) 0.61-0.70 (m, 4H) 0.89-0.95 (m, 2H) 1.43 (d, J=6.82 Hz, 3H) 2.03-2.12 (m, 1H) 2.40-2.49 (m, 4H) 2.76-2.83 (m, 1H) 3.19-3.26 (m, 4 H) 3.37 (br. s., 2H) 4.64 (q, J=6.82 Hz, 1H) 6.41 (d, J=1.52 Hz, 1H) 6.67-6.73 (m, 1H) 6.91 (m, J=8.84 Hz, 2H) 7.70 (m, J=8.59 Hz, 2H) 8.17 (d, J=3.54 Hz, 1H) 10.57 (s, 1H). ESI-MS: m/z 461.4 (M+H)+. mp=202.5-207.3° C.

Sources & evidence

ORD record
ord-6b1c88a0a1e04a08803008c53bdc72f9
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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