9h-Carbazole-1-carboxylic acid → N-[3-(1,2,4-triazol-1-yl)-phenyl]-9H-carbazole-1-carboxamide

HRID 1835450Notes

Reaction equation

HRID 1835450 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.OS1C2C=CC=CC=2N=C1.Cl.C(N=C=NCCCN(C)C)C.[N:39]1([C:44]2[CH:45]=[C:46]([CH:48]=[CH:49][CH:50]=2)[NH2:47])[CH:43]=[N:42][CH:41]=[N:40]1>ClCCl.CN(C)C1C=CN=CC=1>[N:39]1([C:44]2[CH:45]=[C:46]([NH:47][C:14]([C:1]3[C:13]4[NH:12][C:11]5[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=5)[C:5]=4[CH:4]=[CH:3][CH:2]=3)=[O:16])[CH:48]=[CH:49][CH:50]=2)[CH:43]=[N:42][CH:41]=[N:40]1

Participants

7

Reactant 4

HCID 2389249h-Carbazole-1-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 235036563-(1H-1,2,4-Triazol-1-yl)anilineHCID 178527226HCID 178527226, compound

Product 1

HCID 23503658N-[3-(1,2,4-triazol-1-yl)-phenyl]-9H-carbazole-1-carboxamideYield 41.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 9H-carbazole-1-carboxylic acid (148 mg) and 1-hydroxybenzothiazole (114 mg) in dichloromethane (3 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (201 mg) and the mixture was stirred for 15 minutes. After adding 3-(1,2,4-triazol-1-yl)aniline (123 mg) and 4-dimethylaminopyridine (128 mg), the mixture was stirred for 24 hours. The mixture was evaporated under reduced pressure and purified by a silica gel column chromatography eluting with 2% methanol in dichloromethane to give N-[3-(1,2,4-triazol-1-yl)-phenyl]-9H-carbazole-1-carboxamide (103 mg, 41.5%).

Workup

  1. stirringthe mixture was stirred for 24 hours
  2. customThe mixture 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-df7052b2c49f4b7486929b1f93185364
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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