Hydrochloric Acid → HCID 86707396, compound

HRID 878787Notes

Reaction equation

HRID 878787 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([F:14])[C:5]2[S:9][C:8]([C:10](O)=[O:11])=[CH:7][C:6]=2[CH:13]=1.Cl.[CH3:16][NH:17][O:18][CH3:19].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([F:14])[C:5]2[S:9][C:8]([C:10]([N:17]([O:18][CH3:19])[CH3:16])=[O:11])=[CH:7][C:6]=2[CH:13]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59341417HCID 59341417, compound

Product 1

HCID 86707396HCID 86707396, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5,7-difluoro-1-benzothiophene-2-carboxylic acid (synthesized by the method of WO2003/055878, 1.95 g, 9.10 mmol), N,O-dimethylhydroxyamine hydrochloride (977 mg, 10.0 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (1.92 g, 10.0 mmol) and N-hydroxybenzotriazole (1.35 g, 10.0 mmol) in dichloromethane (20 mL) was added triethylamine (1.90 mL, 13.7 mmol) at room temperature. The mixture was stirred at room temperature overnight, and then to the reaction solution was added 10% hydrochloric acid solution, and the mixture was extracted with chloroform. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a crude 5,7-difluoro-N-methoxy-N-methyl-1-benzothiophene-2-carboxamide (2.48 g) as a colorless solid. The resultant was used in the next step without further purification.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7a528dd9116a4160808e0542571e0835
Source dataset
uspto-grants-2015_03
Patent number
US08987445B2

Reaction notes

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