Ammonia → HCID 57901869, compound

HRID 1851580Notes

Reaction equation

HRID 1851580 reaction equation
[CH3:1][N:2]([C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:22]=1[NH:21][C:20]([C:23]1[S:24][CH:25]=[CH:26][N:27]=1)=[CH:19]2)[S:3]([C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:11](O)=[O:12])(=[O:5])=[O:4].[N:28]1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.N.Cl>CN(C)C=O>[CH3:1][N:2]([C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:22]=1[NH:21][C:20]([C:23]1[S:24][CH:25]=[CH:26][N:27]=1)=[CH:19]2)[S:3]([C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:11]([NH2:28])=[O:12])(=[O:4])=[O:5]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57901570HCID 57901570, compound

Product 1

HCID 57901869HCID 57901869, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-({methyl[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]amino}sulfonyl)thiophene-2-carboxylic acid (100 mg), 1H-1,2,3-benzotriazol-1-ol (46 mg) and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (58 mg) in N,N-dimethylformamide (2 mL) was added 28% aqueous ammonia (1 mL), and the mixture was stirred at room temperature for 12 hr. To the reaction mixture was added 1N hydrochloric acid was added, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was crystallized from diethyl ether-hexane to give the title compound (57 mg, yield 57%) as colorless crystals. melting point 269° C.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe obtained residue was crystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-1fe5b6905adc4273b386e2ec6915eb6a
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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