Dichloromethane → 4-(6-(3,5-dimethylisoxazol-4-yl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-4-yl)cinnoline-3-carboxylic acid

HRID 1773701Notes

Reaction equation

[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9](B3OC(C)(C)C(C)(C)O3)[C:10]3[NH:14][C:13](=[O:15])[NH:12][C:11]=3[CH:16]=2)=[C:5]([CH3:26])[O:4][N:3]=1.Cl[C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=[N:30][C:29]=1[C:38]([O:40]C)=[O:39].C(Cl)Cl.N1(C2CCCCCCCCCC2)CCCN=CCCCCC1>CS(C)=O.O>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:28]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:31]=[N:30][C:29]=3[C:38]([OH:40])=[O:39])[C:10]3[NH:14][C:13](=[O:15])[NH:12][C:11]=3[CH:16]=2)=[C:5]([CH3:26])[O:4][N:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 6-(3,5-dimethylisoxazol-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-one (100.0 mg, 0.282 mmol) and methyl 4-chlorocinnoline-3-carboxylate (94.0 mg, 0.422 mmol) was treated with PdCl2dppf.CH2Cl2 (20.6 mg, 0.028 mmol) in the presence of 1,8-Diazabicycloundec-7-ene (DBU, 300.0 mg, 1.971 mmol, 7.0 equiv) in DMSO (1 mL) and water (1 mL). The reaction mixture was heated at 110° C. for 12 min in oil bath. The reaction mixture was purified by HPLC to give 4-(6-(3,5-dimethylisoxazol-4-yl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-4-yl)cinnoline-3-carboxylic acid.

Workup

customThe reaction mixture was purified by HPLC

Sources & evidence

ORD record: ord-8dca494211ba4b35afaa07693e375de4
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255089B2

Reaction notes

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