1-Hydroxybenzotriazole → N-[6-methyl-3-(pyrimidin-5-yl)-phenyl]-9H-carbazole-1-carboxamide

HRID 1835456Notes

Reaction equation

HRID 1835456 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.ON1C2C=CC=CC=2N=N1.[NH2:27][C:28]1[CH:29]=[C:30]([C:35]2[CH:36]=[N:37][CH:38]=[N:39][CH:40]=2)[CH:31]=[CH:32][C:33]=1[CH3:34]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:34][C:33]1[C:28]([NH:27][C:14]([C:1]2[C:13]3[NH:12][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5]=3[CH:4]=[CH:3][CH:2]=2)=[O:16])=[CH:29][C:30]([C:35]2[CH:40]=[N:39][CH:38]=[N:37][CH:36]=2)=[CH:31][CH:32]=1

Participants

6

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 2389249h-Carbazole-1-carboxylic acidHCID 235036782-Methyl-5-(pyrimidin-5-YL)aniline

Product 1

HCID 23503655N-[6-methyl-3-(pyrimidin-5-yl)-phenyl]-9H-carbazole-1-carboxamideYield 33.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 9H-carbazole-1-carboxylic acid (148 mg) and 1-hydroxybenzotriazole (114 mg) in dichloromethane (3 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiinide hydrochloride (201 mg), and the m e was stirred for 15 minutes. After adding 5-(3-amino-4-methylphenyl)pyrimdine (136 mg) and 4dimethylaminopyridine (128 mg), the mixture was stirred for 24 hours. The mixture was evaporated under reduced pressure and the residue was purified by a silica gel column chromatography eluting with 2% methanol in dichloromethane to give N-[6methyl-3-(pyrimidin-5-yl)-phenyl]-9H-carbazole-1-carboxamide (89 mg, 33.6%).

Workup

  1. stirringthe mixture was stirred for 24 hours
  2. customThe mixture was evaporated under reduced pressure
  3. customthe residue was purified by a silica gel column chromatography
  4. washeluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-7c0ca8d3190d472998aa282b57a2539f
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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