Hydrazine hydrate (1:1) → HCID 57901816, compound

HRID 1851432Notes

Reaction equation

HRID 1851432 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].[N:22]1(O)C2C=CC=CC=2N=[N:23]1.Cl.CN(C)CCCN=C=NCC.O.NN>O.CN(C)C=O>[NH:22]([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])[NH2:23]

Participants

7

Reactant 4

HCID 24654Hydrazine hydrate (1:1)HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57476168HCID 57476168, compound

Product 1

HCID 57901816HCID 57901816, compoundYield 44.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acid (0.60 g), 1H-1,2,3-benzotriazol-1-ol (0.28 g) and N,N-dimethylformamide (6 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.40 g) at room temperature. The mixture was stirred for 10 min and hydrazine monohydrate (0.28 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 dried to give the title compound (0.28 g, yield 44%) as colorless crystals. melting point>276° C. (decomposition).

Workup

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

Sources & evidence

ORD record
ord-3029cc3f760d42b89b90a2bbd4cd21f9
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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