N-cyclopropyl-3-methyl-4-(piperazin-1-yl)benzamide dihydrochloride → HCID 66716876, compound

HRID 1184518Notes

Reaction equation

HRID 1184518 reaction equation
[CH2:1]([O:3][C:4]1[C:9]2[O:10][CH:11]([CH3:15])[C:12](=[O:14])[NH:13][C:8]=2[CH:7]=[C:6]([CH:16]=O)[CH:5]=1)[CH3:2].Cl.Cl.[CH:20]1([NH:23][C:24](=[O:38])[C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)=[C:27]([CH3:37])[CH:26]=2)[CH2:22][CH2:21]1>>[CH:20]1([NH:23][C:24](=[O:38])[C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH2:32][CH2:33][N:34]([CH2:16][C:6]4[CH:5]=[C:4]([O:3][CH2:1][CH3:2])[C:9]5[O:10][CH:11]([CH3:15])[C:12](=[O:14])[NH:13][C:8]=5[CH:7]=4)[CH2:35][CH2:36]3)=[C:27]([CH3:37])[CH:26]=2)[CH2:22][CH2:21]1

Participants

3

Reactant 2

HCID 66775049N-cyclopropyl-3-methyl-4-(piperazin-1-yl)benzamide dihydrochlorideHCID 718134828-Ethoxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde

Product 1

HCID 66716876HCID 66716876, compound

Procedure

Using 398B and N-cyclopropyl-3-methyl-4-(piperazin-1-yl)benzamide-2HCl in the general procedure for reductive aminations, the title compound was obtained as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 0.51-0.57 (m, 2H) 0.63-0.70 (m, 2H) 1.33 (t, J=7.07 Hz, 3H) 1.41 (d, J=6.82 Hz, 3H) 2.25 (s, 3 H) 2.52-2.60 (m, 4H) 2.81 (td, J=7.26, 3.92 Hz, 1H) 2.89 (br. s., 4H) 3.42 (s, 2H) 3.98-4.10 (m, 2H) 4.54-4.66 (m, 1H) 6.51 (d, J=1.52 Hz, 1H) 6.63 (d, J=1.77 Hz, 1H) 7.01 (d, J=8.08 Hz, 1H) 7.55-7.66 (m, 2H) 8.23 (d, J=4.04 Hz, 1H) 10.57 (s, 1H). ESI-MS: m/z 479.5 (M+H)+. mp 223.4-223.5° C.

Sources & evidence

ORD record
ord-d6775b7b5f414221b25c7f4768d22283
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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