1,2,3,4-Tetrahydro-1-naphthylamine → 10-{[(4-Bromophenyl)thio]acetyl}-N-(1,2,3,4-tetrahydronaphthalen-1-YL)-10,11-dihydro-5H-pyrrolo[2,1-C][1,4]benzodiazepine-3-carboxamide

HRID 639291Notes

Reaction equation

HRID 639291 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][S:21][C:22]3[CH:27]=[CH:26][C:25]([Br: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].[CH:32]1([NH2:42])[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:35][CH2:34][CH2:33]1>>[Br:28][C:25]1[CH:24]=[CH:23][C:22]([S: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:42][CH:32]4[C:41]5[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=5)[CH2:35][CH2:34][CH2:33]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 180661,2,3,4-Tetrahydro-1-naphthylamineHCID 160393672,2,2-trichloro-1-[10-{[(4-bromophenyl)thio]acetyl}-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-yl]-ethanone

Product 1

HCID 1603944310-{[(4-Bromophenyl)thio]acetyl}-N-(1,2,3,4-tetrahydronaphthalen-1-YL)-10,11-dihydro-5H-pyrrolo[2,1-C][1,4]benzodiazepine-3-carboxamide

Procedure

The title compound was synthesized in the manner of Example 81 from 2,2,2-trichloro-1-[10-{[(4-bromophenyl)thio]acetyl}-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-yl]-ethanone of Example 80 and 1,2,3,4-tetrahydronaphthalen-1-ylamine, m.p. 163-165° C. MS [(+)ESI, m/z]: 586 [M+H]+

Sources & evidence

ORD record
ord-a17256946c4641f2b3e6ab3f333d6214
Source dataset
uspto-grants-2010_04
Patent number
US07691848B2

Reaction notes

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