2-Chlorobenzimidazole → HCID 71208992, compound

HRID 1887948Notes

Reaction equation

HRID 1887948 reaction equation
[NH2:1][CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([Cl:14])=[CH:9][CH:10]=2)[N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:4]=1.C(N(CC)C(C)C)(C)C.Cl[C:31]1[NH:32][C:33]2[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=2[N:35]=1>CN1C(=O)CCC1>[NH:32]1[C:33]2[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=2[N:35]=[C:31]1[NH:1][CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([Cl:14])=[CH:9][CH:10]=2)[N:5]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 785722-ChlorobenzimidazoleHCID 81531DiisopropylethylamineHCID 712083983-(aminomethyl)-7-chloro-1-phenylquinolin-4(1H)-one2×

Product 1

HCID 71208992HCID 71208992, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 3-(aminomethyl)-7-chloro-1-phenylquinolin-4(1H)-one (intermediate D) (40 mg, 0.140 mmol), N,N-diisopropylethylamine (74.0 mg, 100 μL, 0.570 mmol) and 2-chlorobenzimidazole (29 mg, 0.186 mmol) in NMP (500 μL) was heated at 115° C. in a sealed tube overnight. After this time, very little desired product was observed via LC/MS. Additional 2-chlorobenzimidazole (30 mg, 0.196 mmol), N,N-diisopropylethylamine (74.0 mg, 100 μL, 0.570 mmol), and NMP (0.2 mL) were added, and the reaction mixture was transferred to a small microwave tube. The mixture was heated via microwave irradiation at 180° C. for 2 hr. The reaction mixture was concentrated under a stream of nitrogen, and the crude product was purified by preparative reverse-phase HPLC. The product 3-[(1H-Benzoimidazol-2-ylamino)-methyl]-7-chloro-1-phenyl-1H-quinolin-4-one (4 mg, 6.8%) was obtained as an off-white solid. MS calcd. for C23H17ClN4O [(M+H)+] 401.1, obsd. 401.

Sources & evidence

ORD record
ord-d4a9eeb690ab444b8fd64266532b53cb
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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