1-Hydroxybenzotriazole → HCID 57901617, compound

HRID 1851487Notes

Reaction equation

HRID 1851487 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[C:34]([NH:35][S:36]([C:39]2[S:40][CH:41]=[CH:42][CH:43]=2)(=[O:38])=[O:37])=[C:33]2[C:29]([CH:30]=[C:31]([C:44](O)=[O:45])[NH:32]2)=[CH:28][CH:27]=1.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[C:34]([NH:35][S:36]([C:39]2[S:40][CH:41]=[CH:42][CH:43]=2)(=[O:38])=[O:37])=[C:33]2[C:29]([CH:30]=[C:31]([C:44]([NH:24][CH2:23][CH2:22][S:21][C:2]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[O:45])[NH:32]2)=[CH:28][CH:27]=1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 184272672-(Tritylthio)ethylamine hydrochlorideHCID 57901713HCID 57901713, compound

Product 1

HCID 57901617HCID 57901617, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-(tritylthio)ethylamine hydrochloride (0.44 g), triethylamine (0.17 mL) and N,N-dimethylformamide (15 mL) were added 6-methyl-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acid (0.34 g), 1H-1,2,3-benzotriazol-1-ol (0.21 g) and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.26 g) under ice-cooling, and the mixture was stirred at room temperature for 2 days. 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 (585 mg, yield 91%) as colorless prism crystals. melting point 245-246° 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-e066a8ecf0014c3485114f569c33908c
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

Loading…