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

HRID 1835463Notes

Reaction equation

HRID 1835463 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.[N:17]1([C:22]2[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=2)[NH2:25])[CH:21]=[N:20][N:19]=[CH:18]1.Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1>[N:19]1[N:20]=[CH:21][N:17]([C:22]2[CH:23]=[C:24]([NH:25][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:26]=[CH:27][CH:28]=2)[CH:18]=1

Participants

6

Reactant 3

HCID 2389249h-Carbazole-1-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 64929213-(4H-1,2,4-triazol-4-yl)aniline

Product 1

HCID 23503693N-(3-([1,2,4]triazol-4-yl)phenyl)-9H-carbazole-1-carboxamideYield 20.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 9H-carbazole-1-carboxylic acid (112 mg) and 3-(1,3,4-triazol-1-yl)aniline (147 mg) in dichloromethane (3 ml) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (188 mg) and 4-dimethylaminopyridine (43 mg). The mixture was stirred at ambient temperature for 24 hours and diluted with dichloromethane. The solution was washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated with methanol. The resulting precipitate was collected by filtration and dried to give N-(3-([1,2,4]triazol-4-yl)phenyl)-9H-carbazole-1-carboxamide (38 mg, 15.4%).

Workup

  1. washThe solution was washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was triturated with methanol
  5. filtrationThe resulting precipitate was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-c2002e14caac4919bd4d250d1eda6080
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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