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1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-[3-(2,3-dimethyl-3H-imidazol-4-yl)-phenyl]-4'-fluoro-biphenyl-3-carboxamide

HRID 1835459
Notes
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Reaction equation

HRID 1835459 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=2)[C:11]([OH:13])=O)=[CH:4][CH:3]=1.[CH3:17][N:18]1[C:22]([C:23]2[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=2)[NH2:26])=[CH:21][N:20]=[C:19]1[CH3:30].Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1>[CH3:30][C:19]1[N:18]([CH3:17])[C:22]([C:23]2[CH:24]=[C:25]([NH:26][C:11]([C:10]3[CH:9]=[C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[CH:16]=[CH:15][CH:14]=3)=[O:13])[CH:27]=[CH:28][CH:29]=2)=[CH:21][N:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27826883-(4-Fluorophenyl)benzoic acidHCID 235036623-(1,2-dimethyl-1H-imidazol-5-yl)aniline

Product 1

HCID 23503670N-[3-(2,3-dimethyl-3H-imidazol-4-yl)-phenyl]-4'-fluoro-biphenyl-3-carboxamideYield 89.2%

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 3-(4-fluorophenyl)benzoic acid (151 mg) and 3-(1,2-dimethylimidazol-5-yl)aniline (131 mg) in dichloromethane (5 ml) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (201 mg) and 4-dimethylaminopyridine (43 mg). The mixture was stirred at ambient temperature for 18 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 purified by a silica gel column chromatography eluting with 3% methanol in dichloromethane to give N-[3-(2,3 dimethyl-3H-imidazolyl)-phenyl]-4′-fluoro-biphenyl-3-carboxamide (240 mg, 88.9%).

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 purified by a silica gel column chromatography
  5. washeluting with 3% methanol in dichloromethane

Sources & evidence

ORD record
ord-08165f45d7d44ccaab7e957f05c8afcf
Source dataset
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06770667B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes