Succinic Acid → 7-Chloro-6-{4-[2-(cyclopropylmethyl-amino)-thiazol-4-yl]-phenylthiomethyl}-2,3,4,5-tetrahydro-1H-benzo[d]azepine Succinate

HRID 1670578Notes

Reaction equation

HRID 1670578 reaction equation
[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[Cl:9][C:10]1[CH:20]=[CH:19][C:13]2[CH2:14][CH2:15][NH:16][CH2:17][CH2:18][C:12]=2[C:11]=1[CH2:21][S:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[N:30]=[C:31]([NH:34][CH2:35][CH:36]3[CH2:38][CH2:37]3)[S:32][CH:33]=2)=[CH:25][CH:24]=1>C(O)C>[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[Cl:9][C:10]1[CH:20]=[CH:19][C:13]2[CH2:14][CH2:15][NH:16][CH2:17][CH2:18][C:12]=2[C:11]=1[CH2:21][S:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]2[N:30]=[C:31]([NH:34][CH2:35][CH:36]3[CH2:38][CH2:37]3)[S:32][CH:33]=2)=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 1110Succinic AcidHCID 598222837-chloro-6-{4-[2-(cyclopropylmethyl-amino)-thiazol-4-yl]-phenylthiomethyl}-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 866237107-Chloro-6-{4-[2-(cyclopropylmethyl-amino)-thiazol-4-yl]-phenylthiomethyl}-2,3,4,5-tetrahydro-1H-benzo[d]azepine SuccinateYield 99.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add succinic acid (0.053 g, 0.453 mmol) to a mixture of 7-chloro-6-{4-[2-(cyclopropylmethyl-amino)-thiazol-4-yl]-phenylthiomethyl}-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.207 g, 0.452 mmol) in absolute ethanol (10 mL) at room temperature and stir for 1 h. Concentrate the reaction mixture in vacuo. Combine the residue with MTBE (5 mL) and concentrate three times to afford a pale yellow foam. Dry under high vacuum at room temperature overnight to obtain the title compound (0.259 g, 99%) as a pale yellow foam. MS (ES+) m/z: 456.0 (M+H)+.

Workup

  1. concentrationConcentrate the reaction mixture in vacuo
  2. concentrationconcentrate three times
  3. customto afford a pale yellow foam
  4. customDry under high vacuum at room temperature overnight

Sources & evidence

ORD record
ord-b86caadae15a443db9c61e7471ffd126
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

Loading…