1-Hydroxybenzotriazole → 4-Methyl-7-[(2-thienylsulfonyl)amino]-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide

HRID 1851476Notes

Reaction equation

HRID 1851476 reaction equation
Cl.[C:2]([S:21][CH2:22][CH2:23][NH2:24])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:25][C:26]1[CH:34]=[CH:33][C:32]([NH:35][S:36]([C:39]2[S:40][CH:41]=[CH:42][CH:43]=2)(=[O:38])=[O:37])=[C:31]2[C:27]=1[CH:28]=[C:29]([C:44](O)=[O:45])[NH:30]2.N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(OCC)(=O)C.CN(C)C=O.C(N(CC)CC)C>[CH3:25][C:26]1[CH:34]=[CH:33][C:32]([NH:35][S:36]([C:39]2[S:40][CH:41]=[CH:42][CH:43]=2)(=[O:38])=[O:37])=[C:31]2[C:27]=1[CH:28]=[C:29]([C:44]([NH:24][CH2:23][CH2:22][S:21][C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:45])[NH:30]2

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 184272672-(Tritylthio)ethylamine hydrochlorideHCID 579018214-Methyl-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acid

Product 1

HCID 579016404-Methyl-7-[(2-thienylsulfonyl)amino]-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamideYield 95%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-(tritylthio)ethylamine hydrochloride (0.93 g), triethylamine (0.37 mL) and N,N-dimethylformamide (15 mL) were added 4-methyl-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acid (0.73 g), 1H-1,2,3-benzotriazol-1-ol (0.47 g) and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.59 g) under ice-cooling, and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with ethyl acetate, washed with aqueous citric acid solution, aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained crystals were washed with ethyl acetate-hexane to give the title compound (1.31 g, yield 95%) as pale-yellow crystals. melting point 241-242° C.

Workup

  1. temperaturecooling
  2. washwashed with aqueous citric acid solution, aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe obtained crystals were washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-3d53068a219e4e42b4aff4611829e0c5
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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