Ammonia → HCID 57901592, compound

HRID 1851549Notes

Reaction equation

HRID 1851549 reaction equation
[CH3:1][N:2]([S:22]([C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)(=[O:24])=[O:23])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][C:14]([CH2:17][CH2:18][C:19](O)=[O:20])=[CH:15][N:16]=1)=[CH:8]2.[N:30]1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.N>O.CN(C)C=O>[CH3:1][N:2]([S:22]([C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)(=[O:24])=[O:23])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][C:14]([CH2:17][CH2:18][C:19]([NH2:30])=[O:20])=[CH:15][N:16]=1)=[CH:8]2

Participants

7

Reactant 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57901696HCID 57901696, compound

Product 1

HCID 57901592HCID 57901592, compoundYield 127.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-(2-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazol-5-yl)propanoic acid (1.15 g), 1H-1,2,3-benzotriazol-1-ol (0.54 g) and N,N-dimethylformamide (14 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.77 g) at room temperature. The mixture was stirred at room temperature for 1 hr, and 28% aqueous ammonia (1.0 mL) was added. The reaction mixture was stirred at room temperature overnight, and water was added. The resulting crystals were filtrated, washed with water and ethyl acetate, and dried to give the title compound (1.46 g, yield 98%) as yellow crystals. melting point 246-247° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. filtrationThe resulting crystals were filtrated
  3. washwashed with water and ethyl acetate
  4. customdried

Sources & evidence

ORD record
ord-9118c440356540809ae622c59b903d1b
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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