Citric Acid → HCID 57901704, compound

HRID 1851442Notes

Reaction equation

HRID 1851442 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].[NH2:22][C:23]([CH3:27])([CH3:26])[CH2:24][OH:25].N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.CN(C)C=O>[OH:25][CH2:24][C:23]([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])([CH3:27])[CH3:26]

Participants

8

Reactant 5

HCID 311Citric AcidHCID 118072-Amino-2-methyl-1-propanolHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57476168HCID 57476168, compound

Product 1

HCID 57901704HCID 57901704, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acid (1.00 g), 2-amino-2-methylpropan-1-ol (0.55 g), 1H-1,2,3-benzotriazol-1-ol (0.50 g) and N,N-dimethylformamide (15 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.71 g) at 0° C., and the mixture was stirred at 60° C. overnight. Water was added to the reaction mixture and the mixture was acidified with 10% aqueous citric acid solution. The resulting crystals were filtrated, washed with water, and dried to give the title compound (0.89 g, yield 74%) as colorless crystals. melting point>217° C. (decomposition).

Workup

  1. filtrationThe resulting crystals were filtrated
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-9ead23b54cba4c3497a214cca1e550db
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

Loading…