Methyl 4-aminobenzoate → HCID 68699035, compound

HRID 2235127Notes

Reaction equation

HRID 2235127 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19](O)=[O:20])[CH:17]=3)[CH2:12][CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[CH3:26][O:27][C:28](=[O:36])[C:29]1[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=1>ClCCl.CN(C=O)C>[CH3:26][O:27][C:28](=[O:36])[C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:19]([C:16]2[CH:17]=[C:18]3[C:13]([CH2:12][CH2:11][N:10]3[S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])=[CH:14][CH:15]=2)=[O:20])=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 12082Methyl 4-aminobenzoateHCID 24386Thionyl ChlorideHCID 68697185HCID 68697185, compound

Product 1

HCID 68699035HCID 68699035, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Benzenesulfonyl-2,3-dihydro-1H-indole-6-carboxylic acid (40 mg, 0.13 mmol) was added to a solution of thionyl chloride (63 mg, 0.53 mmol, 4 equiv.) in dichloromethane (5 ml) and DMF (1 ml). The reaction mixture was stirred for 2 hours, then the solvent was removed. The crude acyl chloride was redissolved in dichloromethane (5 ml) and treated with 4-amino benzoic acid methyl ester (80 mg, 0.53 mmol, 4 equiv.). The mixture was stirred for 30 min. at room temperature, then the solvent was removed. The residue was purified by flash chromatography, yielding 4-[(1-benzenesulfonyl-2,3-dihydro-1H-indole-6-carbonyl)-amino]-benzoic acid methyl ester as a white solid, 42 mg (73%). MS (ISP): m/e=437.3 (M+H+.), δH (300 MHz; CDCl3) 8.02-8.09 (4H, m), 7.82 (2H, d), 7.77 (2H, d), 7.45-7.61 (4H, m), 7.21 (2H, d), 3.98 (2H, t), 3.92 (3H, s), 2.97 (2H, t).

Workup

  1. customthe solvent was removed
  2. dissolutionThe crude acyl chloride was redissolved in dichloromethane (5 ml)
  3. stirringThe mixture was stirred for 30 min. at room temperature
  4. customthe solvent was removed
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-c8ebf8f35bd7421f924a8718e1bb1c0f
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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