Methanol → HCID 57475957, compound

HRID 1851414Notes

Reaction equation

HRID 1851414 reaction equation
[CH:1]1([CH2:4][N:5]([S:21]([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)(=[O:23])=[O:22])[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:14]=2[N:13](COC)[C:12]([C:18]([NH2:20])=[O:19])=[CH:11]3)[CH2:3][CH2:2]1.O.O.C(O)(=O)C(O)=O.CO>O>[CH:1]1([CH2:4][N:5]([S:21]([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)(=[O:22])=[O:23])[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:14]=2[NH:13][C:12]([C:18]([NH2:20])=[O:19])=[CH:11]3)[CH2:3][CH2:2]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 7-[(cyclopropylmethyl)(2-thienylsulfonyl)amino]-1-(methoxymethyl)-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 further at 90° C. for 14 hr. The reaction mixture was allowed to cool to room temperature. The resulting crystals were collected by filtration, washed successively with water, a diethyl ether-hexane mixture and hexane, and dried to give the title compound (286 mg, yield 81%) as crystals. melting point 229-231° C.

Workup

  1. waitfurther at 90° C. for 14 hr
  2. temperatureto cool to room temperature
  3. filtrationThe resulting crystals were collected by filtration
  4. washwashed successively with water
  5. dry with materiala diethyl ether-hexane mixture and hexane, and dried

Sources & evidence

ORD record
ord-ae9ca336e12c448bb6b82362a3ac54ae
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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