Benzamide, N-cyclopropyl-4-(1-piperazinyl)- → HCID 66716861, compound

HRID 1184486Notes

Reaction equation

HRID 1184486 reaction equation
[CH2:1]([C:8]1[C:13]2[O:14][CH:15]([CH3:19])[C:16](=[O:18])[NH:17][C:12]=2[CH:11]=[C:10]([CH:20]=O)[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:22]1([NH:25][C:26](=[O:39])[C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)=[CH:29][CH:28]=2)[CH2:24][CH2:23]1>>[CH2:1]([C:8]1[C:13]2[O:14][CH:15]([CH3:19])[C:16](=[O:18])[NH:17][C:12]=2[CH:11]=[C:10]([CH2:20][N:36]2[CH2:35][CH2:34][N:33]([C:30]3[CH:29]=[CH:28][C:27]([C:26]([NH:25][CH:22]4[CH2:24][CH2:23]4)=[O:39])=[CH:32][CH:31]=3)[CH2:38][CH2:37]2)[CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 28749052Benzamide, N-cyclopropyl-4-(1-piperazinyl)-HCID 86664223HCID 86664223, compound

Product 1

HCID 66716861HCID 66716861, compound

Procedure

Using 353A and N-cyclopropyl-4-(piperazin-1-yl)benzamide 284 in the general procedure for reductive aminations, the title compound was obtained as a light grey solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 0.49-0.55 (m, 2H) 0.62-0.69 (m, 2H) 1.31 (d, J=6.82 Hz, 3H) 2.42-2.49 (m, 4H) 2.75-2.82 (m, 1H) 3.17-3.25 (m, 4H) 3.38 (s, 2H) 3.89 (s, 2H) 4.57 (q, J=6.74 Hz, 1H) 6.73-6.82 (m, 2 H) 6.91 (d, J=9.09 Hz, 2H) 7.14-7.19 (m, 1H) 7.19-7.24 (m, 2H) 7.24-7.30 (m, 2H) 7.69 (d, J=9.09 Hz, 2H) 8.14 (d, J=4.04 Hz, 1H) 10.60 (s, 1H). ESI-MS: m/z 511.4 (M+H)+. mp=192.3-203.2° C.

Sources & evidence

ORD record
ord-bec967d36c0a424e941549e61c6b6b7b
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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