2-Pyridineethanethioamide, hydrochloride (1:1) → 4'-[[2-(2-pyridylmethyl)-5,6-dihydro-4H-thiazolo[5,4-d][1]benzazepin-6-yl)carbonyl]-2-phenylbenzanilide

HRID 1342Notes

Reaction equation

HRID 1342 reaction equation
[C:1]1([C:7]2[CH:35]=[CH:34][CH:33]=[CH:32][C:8]=2[C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([N:20]3[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[C:24](=O)[CH2:23][CH2:22][CH2:21]3)=[O:19])=[CH:14][CH:13]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[N:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[CH2:43][C:44]([NH2:46])=[S:45]>>[N:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[CH2:43][C:44]1[S:45][C:23]2[CH2:22][CH2:21][N:20]([C:18]([C:15]3[CH:16]=[CH:17][C:12]([NH:11][C:9](=[O:10])[C:8]4[CH:32]=[CH:33][CH:34]=[CH:35][C:7]=4[C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:13][CH:14]=3)=[O:19])[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[C:24]=2[N:46]=1

Participants

3

Reactant 2

HCID 30351622-Pyridineethanethioamide, hydrochloride (1:1)HCID 11798200N-[4-(5-oxo-3,4-dihydro-2H-1-benzazepine-1-carbonyl)phenyl]-2-phenylbenzamide

Product 1

HCID 106986974'-[[2-(2-pyridylmethyl)-5,6-dihydro-4H-thiazolo[5,4-d][1]benzazepin-6-yl)carbonyl]-2-phenylbenzanilideYield 58.3%

Procedure

Using 400 mg of 2-phenyl-4'-[(5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonyl]benzanilide and 370 mg of 2-pyridylthioacetamide hydrochloride, the procedure of Example 5 was repeated, and the resulting free base was recrystallized from chloroform-diethyl ether to obtain 300 mg of 4'-[[2-(2-pyridylmethyl)-5,6-dihydro-4H-thiazolo[5,4-d][1]benzazepin-6-yl)carbonyl]-2-phenylbenzanilide.

Workup

  1. customthe resulting free base was recrystallized from chloroform-diethyl ether

Sources & evidence

ORD record
ord-a89ffbbd03274d85a4403eaa7a25775f
Source dataset
uspto-grants-1998_03
Patent number
US05723606

Reaction notes

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