Potassium Hydroxide → HCID 68351413, compound

HRID 2401146Notes

Reaction equation

[OH-].[K+].[C:3]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]3[N:15]=[C:16]([O:18][C:19]4[CH:20]=[CH:21][C:22]([CH3:29])=[C:23]([CH:28]=4)[C:24]([O:26]C)=[O:25])[NH:17][C:12]3=[CH:11][C:10]=2[Cl:30])=[CH:5][CH:4]=1>CO>[C:3]1([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:4]=[CH:5][C:6]([C:9]2[N:14]=[C:13]3[N:15]=[C:16]([O:18][C:19]4[CH:20]=[CH:21][C:22]([CH3:29])=[C:23]([CH:28]=4)[C:24]([OH:26])=[O:25])[NH:17][C:12]3=[CH:11][C:10]=2[Cl:30])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2N KOH (1.1 mL, 2.2 mmol) was added to a methanol (10 mL) solution of methyl 5-{[5-(biphenyl-4-yl)-6-chloro-1-H imidazo[4,5-b]pyridin-2-yl]oxy}-2-methylbenzoate (104 mg, 0.22 mmol) and the reaction was stirred at 80° C. for 2 h. The reaction was partitioned between EtOAc and 10% aqueous citric acid. The organic layer was separated, washed with brine, dried over magnesium sulfate and concentrated. Flash chromatography of the resulting residue utilizing a Biotage™ 10G SNAP cartridge and employing a gradient: 0-100% EtOAc/hexane afforded the title compound as a white solid. LC-MS: calculated for C26H18ClN3O3 455.89, observed m/e: 456.2 (M+H)+ (Rt 2.0/4 min). 1H NMR δ (ppm) (DMSO-d6): 8.00 (1H, s), 7.82 (1H, m) 7.79-7.69 (7H, m), 7.48 (2H, m), 7.38 (2H, m), 2.56 (3H, s).

Workup

customThe reaction was partitioned between EtOAc and 10% aqueous citric acid
customThe organic layer was separated
washwashed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-271e61ff51ae4a7f9e22f47b75e79729
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796258B2

Reaction notes

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