Citric Acid → HCID 57901701, compound

HRID 1851603Notes

Reaction equation

HRID 1851603 reaction equation
[CH2:1]([N:3]([C:12]1[CH:13]=[C:14]([CH3:29])[C:15]([CH3:28])=[C:16]2[C:20]=1[NH:19][C:18]([C:21]1[S:22][C:23]([CH:26]=[O:27])=[CH:24][N:25]=1)=[CH:17]2)[S:4]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)(=[O:6])=[O:5])[CH3:2].CO.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[CH2:1]([N:3]([C:12]1[CH:13]=[C:14]([CH3:29])[C:15]([CH3:28])=[C:16]2[C:20]=1[NH:19][C:18]([C:21]1[S:22][C:23]([CH2:26][OH:27])=[CH:24][N:25]=1)=[CH:17]2)[S:4]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:6])[CH3:2]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 57901603HCID 57901603, compound

Product 1

HCID 57901701HCID 57901701, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixed solution of N-ethyl-N-[2-(5-formyl-1,3-thiazol-2-yl)-4,5-dimethyl-1H-indol-7-yl]thiophene-2-sulfonamide (85 mg), methanol (10 mL) and tetrahydrofuran (15 mL) was added sodium borohydride (10 mg) under ice-cooling, and the mixture was stirred at the same temperature for 2 hr. Aqueous citric acid solution was added to the reaction mixture, and the organic solvent was evaporated under reduced pressure. The obtained mixture was extracted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained crystals were washed with ethyl acetate-hexane to give the title compound (84 mg, yield 99%) as pale-yellow crystals, melting point 189-190° C.

Workup

  1. temperaturecooling
  2. customthe organic solvent was evaporated under reduced pressure
  3. extractionThe obtained mixture was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washThe obtained crystals were washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-848701aa0f4d4923bc485a3707db263c
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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