Ammonia → 4-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide

HRID 504654Notes

Reaction equation

HRID 504654 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]([CH3:20])[S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:14])=[O:13])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:21]([OH:23])=O)[NH:6]2.[N:24]1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.N>CN(C)C=O>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]([CH3:20])[S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:14])=[O:13])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:21]([NH2:24])=[O:23])[NH:6]2

Participants

6

Reactant 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574760074-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acid

Product 1

HCID 574760064-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxamideYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acid (2.2 g), 1H-1,2,3-benzotriazol-1-ol (1.2 g), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (1.5 g) and N,N-dimethylformamide (30 ml) was stirred at room temperature for 1 hr, and then at 60° C. for 1 hr. 28% Aqueous ammonia (2.0 ml) was added to the reaction solution, and the mixture was stirred at room temperature for 3 hr. The reaction solution was concentrated under reduced pressure, and the obtained residue was diluted with ethyl acetate. The mixture was washed with water, aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained oil was crystallized from ethyl acetate-hexane to give the title compound (1.84 g, yield 84%) as colorless prism crystals. melting point 221-222° C.

Workup

  1. waitat 60° C. for 1 hr
  2. stirringthe mixture was stirred at room temperature for 3 hr
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additionthe obtained residue was diluted with ethyl acetate
  5. washThe mixture was washed with water, aqueous sodium hydrogencarbonate solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained oil was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-745087227ec34ad0ac612eecf94e2d58
Source dataset
uspto-grants-2010_08
Patent number
US07777047B2

Reaction notes

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