1-Hydroxybenzotriazole → 7-{[(5-Chloro-2-thienyl)sulfonyl]amino}-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide

HRID 1851450Notes

Reaction equation

HRID 1851450 reaction equation
[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C:11]2[CH:12]=[CH:13][CH:14]=[C:15]3[C:19]=2[NH:18][C:17]([C:20](O)=[O:21])=[CH:16]3)(=[O:9])=[O:8])=[CH:4][CH:3]=1.Cl.[C:24]([S:43][CH2:44][CH2:45][NH2:46])([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>O.CN(C)C=O.C(N(CC)CC)C>[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C:11]2[CH:12]=[CH:13][CH:14]=[C:15]3[C:19]=2[NH:18][C:17]([C:20]([NH:46][CH2:45][CH2:44][S:43][C:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:21])=[CH:16]3)(=[O:8])=[O:9])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 184272672-(Tritylthio)ethylamine hydrochlorideHCID 579018287-{[(5-Chloro-2-thienyl)sulfonyl]amino}-1H-indole-2-carboxylic acid

Product 1

HCID 579017477-{[(5-Chloro-2-thienyl)sulfonyl]amino}-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamideYield 97%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 7-{[(5-chloro-2-thienyl)sulfonyl]amino}-1H-indole-2-carboxylic acid (0.84 g), 2-(tritylthio)ethylamine hydrochloride (0.85 g), 1H-1,2,3-benzotriazol-1-ol (0.35 g), triethylamine (0.36 mL) and N,N-dimethylformamide (20 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.50 g) at 0° C., and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the obtained crystals were filtrated, washed with water and dried. The obtained crystals were subjected to silica gel column chromatography and the title compound (1.41 g, yield 97%) was obtained as colorless crystals from a fraction eluted with ethyl acetate. melting point>197° C. (decomposition).

Workup

  1. filtrationthe obtained crystals were filtrated
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-ad02b18ea112423cbe005fbae01f741e
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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