Ammonia → HCID 57476311, compound

HRID 1960347Notes

Reaction equation

HRID 1960347 reaction equation
[CH3:1][N:2]([S:15]([C:18]1[S:19][CH:20]=[CH:21][N:22]=1)(=[O:17])=[O:16])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12](O)=[O:13])=[CH:8]2.[N:23]1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.N>C(OCC)(=O)C.O.CN(C)C=O>[CH3:1][N:2]([S:15]([C:18]1[S:19][CH:20]=[CH:21][N:22]=1)(=[O:17])=[O:16])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([NH2:23])=[O:13])=[CH:8]2

Participants

8

Reactant 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57476154HCID 57476154, compound

Product 1

HCID 57476311HCID 57476311, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 7-[methyl(1,3-thiazol-2-ylsulfonyl)amino]-1H-indole-2-carboxylic acid (1.65 g), 1H-1,2,3-benzotriazol-1-ol (991 mg), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (1.41 g) and N,N-dimethylformamide (10 mL) was stirred at 60° C. for 30 min. The mixture was cooled to 0° C., 28% aqueous ammonia (600 μL) was added, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate (200 mL) and water (200 mL). The organic layer was washed with saturated brine (200 mL), dried over sodium sulfate, and filtrated, and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography with 50% ethyl acetate-hexane mixture as an eluate to give the title compound (1.30 g, yield 79%) as a white solid. melting point 220-221° C.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringthe mixture was stirred overnight at room temperature
  3. washThe organic layer was washed with saturated brine (200 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltrated
  6. concentrationthe filtrate was concentrated
  7. customThe obtained residue was purified by silica gel column chromatography with 50% ethyl acetate-hexane mixture as an eluate

Sources & evidence

ORD record
ord-2442609e04e84b32ad57b23fdca2efa3
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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