1-Hydroxybenzotriazole → HCID 57901645, compound

HRID 1851511Notes

Reaction equation

HRID 1851511 reaction equation
[CH2:1]([N:3]([S:16]([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)(=[O:18])=[O:17])[C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([OH:15])=O)=[CH:9]2)[CH3:2].Cl.[C:25]([S:44][CH2:45][CH2:46][NH2:47])([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>O.CN(C)C=O.C(N(CC)CC)C>[CH2:1]([N:3]([S:16]([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)(=[O:17])=[O:18])[C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([NH:47][CH2:46][CH2:45][S:44][C:25]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:15])=[CH:9]2)[CH3:2]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 184272672-(Tritylthio)ethylamine hydrochlorideHCID 57901762HCID 57901762, compound

Product 1

HCID 57901645HCID 57901645, compoundYield 111.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 7-[ethyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acid (0.43 g), 2-(tritylthio)ethylamine hydrochloride (0.47 g), 1H-1,2,3-benzotriazol-1-ol (0.19 g), triethylamine (0.20 mL) and N,N-dimethylformamide (10 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.28 g) at 0° C., and the mixture was stirred at 50° C. for 1 hr. Water was added to the reaction mixture, and the obtained crystals were filtrated, washed with water and dried to give the title compound (0.89 g, quantitative) as colorless crystals. melting point 58-61° C.

Workup

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

Sources & evidence

ORD record
ord-28af25cacee4419fafc8a6cb25ca3f21
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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