1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-[3-(1,2-dimethylimidazol-5-yl)-phenyl]-6-fluoro-9H-carbazole-1-carboxamide

HRID 1835483Notes

Reaction equation

HRID 1835483 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[C:9]([C:15]([OH:17])=O)=[CH:8][CH:7]=[CH:6][C:5]2=1.[CH3:18][N:19]1[C:23]([C:24]2[CH:25]=[C:26]([CH:28]=[CH:29][CH:30]=2)[NH2:27])=[CH:22][N:21]=[C:20]1[CH3:31].Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1>[CH3:18][N:19]1[C:23]([C:24]2[CH:25]=[C:26]([NH:27][C:15]([C:9]3[C:10]4[NH:11][C:12]5[C:4](=[CH:3][C:2]([F:1])=[CH:14][CH:13]=5)[C:5]=4[CH:6]=[CH:7][CH:8]=3)=[O:17])[CH:28]=[CH:29][CH:30]=2)=[CH:22][N:21]=[C:20]1[CH3:31]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 235036506-fluoro-9H-carbazole-1-carboxylic acidHCID 235036623-(1,2-dimethyl-1H-imidazol-5-yl)aniline

Product 1

HCID 23503681N-[3-(1,2-dimethylimidazol-5-yl)-phenyl]-6-fluoro-9H-carbazole-1-carboxamideYield 59.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 6-fluoro-9H-carbazole-1-carboxylic acid (37 mg) and 3-(1,2-dimethylimidazol-5-yl)aniline (43 mg) in dichloromethane (1 ml) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (53 mg) and 4-dimethylaminopyridine (11 mg), and the mixture was stirred for 40 hours. The mixture was diluted with dichloromethane and washed with water and brine. The mixture was dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified with a silica gel column chromatography eluting with 2-3% methanol/dichloromethane to give N-[3-(1,2-dimethylimidazol-5-yl)-phenyl]-6-fluoro-9H-carbazole-1-carboxamide (38 mg, 51.4%).

Workup

  1. washwashed with water and brine
  2. dry with materialThe mixture was dried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was purified with a silica gel column chromatography
  5. washeluting with 2-3% methanol/dichloromethane

Sources & evidence

ORD record
ord-aa2236e1e6f84e4f9b3249015993a445
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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