4-Chlorophenyl Isocyanate → (4-Chlorophenylaminocarbonyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine-6-carboxylic acid

HRID 1432551Notes

Reaction equation

HRID 1432551 reaction equation
[S:1]1[C:9]2[CH2:8][CH:7]([C:10]([OH:12])=[O:11])[NH:6][CH2:5][C:4]=2[CH:3]=[CH:2]1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[O:22])=[CH:16][CH:15]=1>CN(C=O)C>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:2]2[S:1][C:9]3[CH2:8][CH:7]([C:10]([OH:12])=[O:11])[NH:6][CH2:5][C:4]=3[CH:3]=2)=[O:22])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 12685848(RS)-6-Carboxy-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

Product 1

HCID 131727718(4-Chlorophenylaminocarbonyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine-6-carboxylic acidYield 21.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the crude sample 4,5,6,7-tetrahydro-thieno[3,2-c]pyridine-6-carboxylic acid (323 mg, 1.77 mmol) in DMF (10 mL), 4-chlorophenyl isocyanate (336 mg, 2.19 mmol) was added. It was stirred at room temperature overnight. After being concentrated in vacuo, the residue was purified by HPLC to give the desired product as a powder (130 mg). MS 337.3 and 339.3 (M+H, Cl pattern)

Workup

  1. concentrationAfter being concentrated in vacuo
  2. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-928ac1d13ae74ac1a86cdd0692047a75
Source dataset
uspto-grants-2009_11
Patent number
US07612089B2

Reaction notes

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