Acetohydrazide → HCID 57901605, compound

HRID 1851515Notes

Reaction equation

HRID 1851515 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]([OH:21])=O)=[CH:15]2)(=[O:8])=[O:7].N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[C:44]([NH:47][NH2:48])(=[O:46])[CH3:45]>O.CN(C)C=O>[C:44]([NH:47][NH:48][C:19]([C:16]1[NH:17][C:18]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[NH:9][S:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)(=[O:7])=[O:8])=[O:21])(=[O:46])[CH3:45]

Participants

7

Reactant 4

HCID 14039AcetohydrazideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57476168HCID 57476168, compound

Product 1

HCID 57901605HCID 57901605, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acid (0.70 g), 1H-1,2,3-benzotriazol-1-ol (0.36 g) and N,N-dimethylformamide (8 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.51 g) at room temperature. The mixture was stirred for 10 min and acetohydrazide (0.33 g) was added. The reaction mixture was stirred at room temperature for 2 hr, and water was added. The resulting crystals were filtrated, washed with water, and dried to give the title compound (0.65 g, yield 77%) as colorless crystals. melting point 254-256° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 hr
  2. filtrationThe resulting crystals were filtrated
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-0eea8df5c6c046a88d52146572f51de9
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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