Methanol → HCID 57475957, compound

HRID 1960243Notes

Reaction equation

HRID 1960243 reaction equation
COC[N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N:13]([CH2:22][CH:23]2[CH2:25][CH2:24]2)[S:14]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)(=[O:16])=[O:15])[CH:6]=[C:5]1[C:26]([NH2:28])=[O:27].O.O.C(O)(=O)C(O)=O.CO>O>[CH:23]1([CH2:22][N:13]([S:14]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)(=[O:15])=[O:16])[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:12]=2[NH:4][C:5]([C:26]([NH2:28])=[O:27])=[CH:6]3)[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 887MethanolHCID 61373Oxalic acid dihydrateHCID 57475956HCID 57475956, compound

Product 1

HCID 57475957HCID 57475957, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-(methoxymethyl)-7-[(cyclopropylmethyl)(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide (390 mg), oxalic acid dihydrate (351 mg), methanol (15 ml) and water (15 ml) was stirred at 70° C. for 1 hr, and then at 90° C. for 14 hr. The reaction mixture was allowed to cool to room temperature, and the resulting crystals were collected by filtration, washed successively with water and diethyl ether-hexane mixture, and dried to give the title compound (286 mg, yield 81%) as crystals. melting point 229-231° C.

Workup

  1. waitat 90° C. for 14 hr
  2. temperatureto cool to room temperature
  3. filtrationthe resulting crystals were collected by filtration
  4. washwashed successively with water and diethyl ether-hexane mixture
  5. customdried

Sources & evidence

ORD record
ord-24a1850044e042099ffc480f84c5f152
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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