1-Hydroxybenzotriazole → 9H-carbazole-1-carboxamide

HRID 1835449Notes

Reaction equation

HRID 1835449 reaction equation
[C:1]1([C:14]([OH:16])=O)[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.O[N:18]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.N1C=C(C2C=C(C=CC=2)N)C=NC=1>ClCCl.CN(C)C1C=CN=CC=1>[C:1]1([C:14]([NH2:18])=[O:16])[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 2389249h-Carbazole-1-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 71620493-Pyrimidin-5-ylaniline

Product 1

HCID 20585749H-carbazole-1-carboxamideYield 74.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 9H-carbazole-1-carboxylic acid (422 mg) and 1-hydroxybenzotriazole (324 mg) in dichloromethane (10 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (575 mg), and the mixture was stirred for 15 minutes. After adding 3-(pyrimidin-5-yl)aniline (360 mg) and 4-dimethylaminopyridine (367 mg), the mixture was stirred for 48 hours. The residue was evaporated under reduced pressure and purified by a silica gel column chromatography eluting with 2% methanol in dichloromethane to give N-(3-i din-5-yl)-phenyl)-9H-carbazole-1-carboxamide (314 mg, 43.1%).

Workup

  1. stirringthe mixture was stirred for 48 hours
  2. customThe residue was evaporated under reduced pressure
  3. custompurified by a silica gel column chromatography
  4. washeluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-0dee676d19ee4ec3b5b2ee5737dd97b7
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

Loading…