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

HRID 1670569Notes

Reaction equation

HRID 1670569 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10][C:4]=2[C:3]=1[CH2:13][S:14][C:15]1[S:19][C:18]([NH:20][CH2:21][CH:22]2[CH2:24][CH2:23]2)=[N:17][CH:16]=1.[C:25]([OH:32])(=[O:31])[CH2:26][CH2:27][C:28]([OH:30])=[O:29]>C(O)C>[C:25]([OH:32])(=[O:31])[CH2:26][CH2:27][C:28]([OH:30])=[O:29].[Cl:1][C:2]1[CH:12]=[CH:11][C:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10][C:4]=2[C:3]=1[CH2:13][S:14][C:15]1[S:19][C:18]([NH:20][CH2:21][CH:22]2[CH2:24][CH2:23]2)=[N:17][CH:16]=1

Participants

4

Reactant 2

HCID 1110Succinic AcidHCID 598222607-chloro-6-[2-(cyclopropylmethyl-amino)-thiazol-5-ylthiomethyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 866237077-Chloro-6-[2-(cyclopropylmethyl-amino)-thiazol-5-ylthiomethyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine SuccinateYield 100.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 7-chloro-6-[2-(cyclopropylmethyl-amino)-thiazol-5-ylthiomethyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.055 g, 0.144 mmol) in absolute ethanol (5 mL) add succinic acid (0.017 g, 0.144 mmol). After acid dissolves, concentrate the reaction mixture in vacuo. Combine the residue with MTBE, concentrate in vacuo several times and dry under high vacuum at room temperature overnight to obtain the title compound (0.072 g, 100%) as a white foam. MS (ES+) m/z: 380.0 (M+H)+.

Workup

  1. concentrationAfter acid dissolves, concentrate the reaction mixture in vacuo
  2. concentrationconcentrate in vacuo several times
  3. customdry under high vacuum at room temperature overnight

Sources & evidence

ORD record
ord-3d0a92f055d748a09f0ee0e730e27f26
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

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