4-Chlorobenzoic Acid → 4-Chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)benzamide

HRID 643004Notes

Reaction equation

HRID 643004 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.Cl.[NH2:46][CH2:47][C:48]1[N:49]=[CH:50][N:51]([C:53]2[CH:58]=[CH:57][C:56]([N:59]3[CH:64]=[CH:63][CH:62]=[CH:61][C:60]3=[O:65])=[CH:55][CH:54]=2)[CH:52]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:46][CH2:47][C:48]2[N:49]=[CH:50][N:51]([C:53]3[CH:54]=[CH:55][C:56]([N:59]4[CH:64]=[CH:63][CH:62]=[CH:61][C:60]4=[O:65])=[CH:57][CH:58]=3)[CH:52]=2)=[O:8])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 63184-Chlorobenzoic AcidHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 669741011-(4-(4-(aminomethyl)-1H-imidazol-1-yl)phenyl)pyridin-2(1H)-one hydrochloride

Product 1

HCID 249872574-Chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)benzamideYield 34.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chlorobenzoic acid (40 mg, 0.26 mmol) and triethylamine (0.150 mL, 1.08 mmol) in DMF (2 mL), BOP (135 mg, 0.30 mmol) was added. After 5 min of stirring, 1-(4-(4-(aminomethyl)-1H-imidazol-1-yl)phenyl)pyridin-2(1H)-one hydrochloride (53 mg, 0.18 mmol) was added. The mixture was stirred at room temperature for 2 h. It was then purified by HPLC to give the titled compound (25 mg). MS 405.1 and 407.1 (M+H, Cl pattern).

Workup

  1. stirringThe mixture was stirred at room temperature for 2 h
  2. customIt was then purified by HPLC

Sources & evidence

ORD record
ord-4e7c5cc9f3944311b2d40e55d77e4b3e
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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