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

HRID 1670581Notes

Reaction equation

HRID 1670581 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][N:24]=1>CO>[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][N:24]=1

Participants

4

Reactant 2

HCID 1110Succinic AcidHCID 598222797-chloro-6-{5-[2-(cyclopropylmethyl-amino)-thiazol-4-yl]-pyridin-2-ylthiomethyl}-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 866237127-Chloro-6-{5-[2-(cyclopropylmethyl-amino)-thiazol-4-yl]-pyridin-2-ylthiomethyl}-2,3,4,5-tetrahydro-1H-benzo[d]azepine SuccinateYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add succinic acid (0.073 g, 0.619 mmol) to a mixture of 7-chloro-6-{5-[2-(cyclopropylmethyl-amino)-thiazol-4-yl]-pyridin-2-ylthiomethyl}-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.282 g, 0.618 mmol) in methanol (5 mL) at room temperature. 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 (0.348 g, 98%) as a pale yellow foam. MS (ES+) m/z: 457.0 (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-d2834045a951443e9802d7b490df2e56
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

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