1-Hydroxybenzotriazole → HCID 57901730, compound

HRID 1851480Notes

Reaction equation

HRID 1851480 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:27]=[C:28]2[C:32](=[C:33]([NH:35][S:36]([C:39]3[S:40][CH:41]=[CH:42][CH:43]=3)(=[O:38])=[O:37])[CH:34]=1)[NH:31][C:30]([C:44](O)=[O:45])=[CH:29]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:27]=[C:28]2[C:32](=[C:33]([NH:35][S:36]([C:39]3[S:40][CH:41]=[CH:42][CH:43]=3)(=[O:38])=[O:37])[CH:34]=1)[NH:31][C:30]([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])=[CH:29]2

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 184272672-(Tritylthio)ethylamine hydrochlorideHCID 57901702HCID 57901702, compound

Product 1

HCID 57901730HCID 57901730, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-(tritylthio)ethylamine hydrochloride (0.77 g), triethylamine (0.31 mL) and N,N-dimethylformamide (20 mL) were added 5-methyl-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acid (0.60 g), 1H-1,2,3-benzotriazol-1-ol (0.36 g) and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.45 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 oil was crystallized from ethyl acetate-hexane to give the title compound (1.07 g, yield 95%) as pale-yellow crystals. melting point 214-215° 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. customThe obtained oil was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-ce81d2831507474a9513da2c7a8217ee
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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