Hydrazine hydrate (1:1) → N-{2-[5-(3-hydrazino-3-oxopropyl)-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-methylthiophene-2-sulfonamide

HRID 1851553Notes

Reaction equation

HRID 1851553 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]([OH:21])=O)=[CH:15][N:16]=1)=[CH:8]2.[N:30]1(O)C2C=CC=CC=2N=[N:31]1.Cl.CN(C)CCCN=C=NCC.O.NN>O.CN(C)C=O>[NH:30]([C:19](=[O:21])[CH2:18][CH2:17][C:14]1[S:13][C:12]([C:9]2[NH:10][C:11]3[C:7]([CH:8]=2)=[CH:6][CH:5]=[CH:4][C:3]=3[N:2]([CH3:1])[S:22]([C:25]2[S:26][CH:27]=[CH:28][CH:29]=2)(=[O:24])=[O:23])=[N:16][CH:15]=1)[NH2:31]

Participants

7

Reactant 4

HCID 24654Hydrazine hydrate (1:1)HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57901696HCID 57901696, compound

Product 1

HCID 57901791N-{2-[5-(3-hydrazino-3-oxopropyl)-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-methylthiophene-2-sulfonamideYield 57%

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 (0.50 g), 1H-1,2,3-benzotriazol-1-ol (0.18 g) and N,N-dimethylformamide (15 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.26 g) at room temperature. The mixture was stirred at room temperature for 1 hr and hydrazine monohydrate (0.28 g) 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 (0.29 g, yield 57%) as yellow crystals. melting point 224-226° C.

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-3a12d45ed5534d18a8574b09604cc439
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

Loading…