1-Hydroxybenzotriazole → HCID 57901721, compound

HRID 1851503Notes

Reaction equation

HRID 1851503 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:23]=1[NH:22][C:21]([C:24](O)=[O:25])=[CH:20]2)(=[O:13])=[O:12])(=[O:4])=[O:3].Cl.[C:28]([S:47][CH2:48][CH2:49][NH2:50])([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>O.CN(C)C=O.C(N(CC)CC)C>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:23]=1[NH:22][C:21]([C:24]([NH:50][CH2:49][CH2:48][S:47][C:28]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:25])=[CH:20]2)(=[O:13])=[O:12])(=[O:3])=[O:4]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 184272672-(Tritylthio)ethylamine hydrochlorideHCID 57901672HCID 57901672, compound

Product 1

HCID 57901721HCID 57901721, compoundYield 100.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 7-{[2-(methylsulfonyl)phenylsulfonyl]amino}-1H-indole-2-carboxylic acid (1.00 g), 2-(tritylthio)ethylamine hydrochloride (0.92 g), 1H-1,2,3-benzotriazol-1-ol (0.41 g), triethylamine (0.42 mL) and N,N-dimethylformamide (15 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.58 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 (1.78 g, quantitative) was obtained as colorless crystals from a fraction eluted with ethyl acetate. melting point 91-93° C.

Workup

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

Sources & evidence

ORD record
ord-c4e672af227942d9b8dcef0c1a791ad8
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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