3-Methylbenzylamine → 10-[(4-Chlorophenoxy)acetyl]-N-(3-methylbenzyl)-10,11-dihydro-5H-pyrrolo[2,1-C][1,4]benzodiazepine-3-carboxamide

HRID 639273Notes

Reaction equation

HRID 639273 reaction equation
ClC(Cl)(Cl)[C:3]([C:5]1[N:14]2[C:8]([CH2:9][N:10]([C:19](=[O:29])[CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13]2)=[CH:7][CH:6]=1)=[O:4].[CH3:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=1)[CH2:36][NH2:37]>>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([O:21][CH2:20][C:19]([N:10]2[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13][N:14]3[C:5]([C:3]([NH:37][CH2:36][C:35]4[CH:38]=[CH:39][CH:40]=[C:33]([CH3:32])[CH:34]=4)=[O:4])=[CH:6][CH:7]=[C:8]3[CH2:9]2)=[O:29])=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 660153-MethylbenzylamineHCID 160392192,2,2-trichloro-1-{10-[(4-chlorophenoxy)acetyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone

Product 1

HCID 1603929110-[(4-Chlorophenoxy)acetyl]-N-(3-methylbenzyl)-10,11-dihydro-5H-pyrrolo[2,1-C][1,4]benzodiazepine-3-carboxamide

Procedure

The title compound was synthesized from 2,2,2-trichloro-1-{10-[(4-chlorophenoxy)acetyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone of Example 67 (0.3 mmol) and 3-methylbenzylamine (2.2 eq.) in the manner of Example 68, m.p. 130-131° C. MS [(+)ESI, m/z]: 500 [M+H]+ Anal. Calcd for C29H26CIN3O3: C, 69.66; H, 5.24; N, 8.40. Found: C, 69.80; H, 5.30; N, 8.42.

Sources & evidence

ORD record
ord-1e16bbb8159d483eb216ce1a8eeac4f2
Source dataset
uspto-grants-2010_04
Patent number
US07691848B2

Reaction notes

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