1-Hydroxybenzotriazole → N-(4-methyl-3-(pyrimidin-5-yl)-phenyl)-9H-carbazole-1-carboxamide

HRID 1835468Notes

Reaction equation

HRID 1835468 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.Cl.C(N=C=NCCCN(C)C)C.[CH3:39][C:40]1[CH:46]=[CH:45][C:43]([NH2:44])=[CH:42][C:41]=1[C:47]1[CH:48]=[N:49][CH:50]=[N:51][CH:52]=1>ClCCl.CN(C)C1C=CN=CC=1>[CH3:39][C:40]1[CH:46]=[CH:45][C:43]([NH:44][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:42][C:41]=1[C:47]1[CH:52]=[N:51][CH:50]=[N:49][CH:48]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 2389249h-Carbazole-1-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 235036604-Methyl-3-(pyrimidin-5-yl)aniline

Product 1

HCID 23503694N-(4-methyl-3-(pyrimidin-5-yl)-phenyl)-9H-carbazole-1-carboxamideYield 52.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 9H-carbazole-1-carboxylic acid (148 mg) and 1-hydroxybenzotriazole (130 mg) in dichloromethane (3 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (201 mg) and the mixture was stirred for 5 minutes. After adding 4-methyl-3-(pyrimidin-5-yl)aniline (130 mg) and 4-dimethylaminopyridine (128 mg), the mixture was stirred for 24 hours. The mixture was diluted with dichloromethane and washed with water and brine. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by a silica gel column chromatography eluting with 2% methanol in dichloromethane to give N-(4-methyl-3-(pyrimidin-5-yl)-phenyl)-9H-carbazole-1-carboxamide (140 mg, 52.8%).

Workup

  1. stirringthe mixture was stirred for 24 hours
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by a silica gel column chromatography
  6. washeluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-b9ecfc09572f4965b7b4bc7e4c2e0675
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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