Succinic Acid → 6-(5-Amino-[1,2,4]thiadiazol-3-ylthiomethyl)-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine Succinate

HRID 1670572Notes

Reaction equation

HRID 1670572 reaction equation
[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[NH2:9][C:10]1[S:14][N:13]=[C:12]([S:15][CH2:16][C:17]2[C:27]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22][C:21]=3[CH:20]=[CH:19][C:18]=2[Cl:28])[N:11]=1>C(O)C.C(Cl)Cl.CO>[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[NH2:9][C:10]1[S:14][N:13]=[C:12]([S:15][CH2:16][C:17]2[C:27]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22][C:21]=3[CH:20]=[CH:19][C:18]=2[Cl:28])[N:11]=1

Participants

6

Reactant 2

HCID 1110Succinic AcidHCID 598223046-(5-amino-[1,2,4]thiadiazol-3-ylthiomethyl)-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 673363136-(5-Amino-[1,2,4]thiadiazol-3-ylthiomethyl)-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine SuccinateYield 100%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Add succinic acid (0.035 g, 0.299 mmol) to a mixture of 6-(5-amino-[1,2,4]thiadiazol-3-ylthiomethyl)-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.098 g, 0.299 mmol) in absolute ethanol (5 mL), DCM (5 mL) and methanol (2 mL) at room temperature. Concentrate the reaction mixture in vacuo. Combine the residue with methanol (5 mL) and DCM (5 mL) and concentrate in vacuo. Combine the residue with MTBE (5 mL) and concentrate three times to afford a white solid. Dry under high vacuum at room temperature overnight to afford the title compound (0.133 g, 100%) as a white solid. MS (ES+) m/z: 327.0 (M+H)+.

Workup

  1. concentrationConcentrate the reaction mixture in vacuo
  2. concentrationconcentrate in vacuo
  3. concentrationCombine the residue with MTBE (5 mL) and concentrate three times
  4. customto afford a white solid
  5. customDry under high vacuum at room temperature overnight

Sources & evidence

ORD record
ord-b6d016e0d83e443d92b557d8353e09fd
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

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