HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Dimethylformamide → 7-(Benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxamide

HRID 1188875
Notes
Print preview

Reaction equation

HRID 1188875 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([O:21][C:22]2[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=2)[CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]([OH:20])=O)=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C[N:34](C)CCCN=C=NCC.[NH4+].ON1C2C=CC=CC=2N=N1.CN(C)C=O>O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([O:21][C:22]2[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:29])=[O:30])=[CH:24][CH:23]=2)[CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]([NH2:34])=[O:20])=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220338091-Hydroxybenzotriazole, ammonium saltHCID 668975467-(Benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylic acid

Product 1

HCID 668976427-(Benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxamide
Yield 100.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7-(benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylic acid (1.59 g), 1-[3-(dimethylamino)propyl-3-ethylcarbodiimide hydrochloride (1.4 g), 1-hydroxybenzotriazole ammonium salt (1.1 g) and N,N-dimethylformamide (40 mL) was stirred at room temperature for 16 hr. Water was added to the reaction solution, and the precipitated solid was collected by filtration, and washed successively with water, ethanol and diethyl ether to give the title compound (1.6 g, yield 100%) as a pale-yellow solid. The pale-yellow solid was recrystallized from N,N-dimethylformamide-water to give pale-yellow crystals. melting point 251-252° C.

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washwashed successively with water, ethanol and diethyl ether

Sources & evidence

ORD record
ord-bf3ad1178fdf493a9866a4455237e50a
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08673942B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes