1-Hydroxybenzotriazole → HCID 57901711, compound

HRID 1851484Notes

Reaction equation

HRID 1851484 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.[CH2:25]([S:28]([C:31]1[CH:39]=[CH:38][C:37]([NH:40][S:41]([C:44]2[S:45][CH:46]=[CH:47][CH:48]=2)(=[O:43])=[O:42])=[C:36]2[C:32]=1[CH:33]=[C:34]([C:49](O)=[O:50])[NH:35]2)(=[O:30])=[O:29])[CH2:26][CH3:27].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>[CH2:25]([S:28]([C:31]1[CH:39]=[CH:38][C:37]([NH:40][S:41]([C:44]2[S:45][CH:46]=[CH:47][CH:48]=2)(=[O:43])=[O:42])=[C:36]2[C:32]=1[CH:33]=[C:34]([C:49]([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:50])[NH:35]2)(=[O:29])=[O:30])[CH2:26][CH3:27]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 184272672-(Tritylthio)ethylamine hydrochlorideHCID 57901861HCID 57901861, compound

Product 1

HCID 57901711HCID 57901711, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-(tritylthio)ethylamine hydrochloride (0.42 g), triethylamine (0.17 mL) and N,N-dimethylformamide (15 mL) were added 4-(propylsulfonyl)-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acid (0.42 g), 1H-1,2,3-benzotriazol-1-ol (0.20 g) and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.25 g) under ice-cooling, and the mixture was stirred at room temperature for 18 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 (690 mg, yield 97%) as pale-yellow prism crystals. melting point 200-201° 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-b4be830d6ac94e089b8505063d71c5c7
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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