Sodium Hydroxide → HCID 59267786, compound

HRID 1945285Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=2)=[CH:4][C:5]2[N:9]=[C:8]([O:10][C:11]3[CH:12]=[CH:13][C:14]([CH3:21])=[C:15]([CH:20]=3)[C:16]([O:18]C)=[O:17])[NH:7][C:6]=2[CH:22]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[C:3]([C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=2)=[CH:4][C:5]2[N:9]=[C:8]([O:10][C:11]3[CH:12]=[CH:13][C:14]([CH3:21])=[C:15]([CH:20]=3)[C:16]([OH:18])=[O:17])[NH:7][C:6]=2[CH:22]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of methyl 5-{[6-chloro-5-(2-naphthyl)-1H-benzimidazol-2-yl]oxy}-2-methylbenzoate in MeOH (3 mL) was added NaOH (2.5 M in water) (0.5 mL, 1 mmol). The mixture was heated at 50° C. and monitored by LC-MS. When the reaction was complete, it was partitioned between EtOAc and 2 M aqueous HCl. The aqueous phase was extracted with EtOAc. The combined organics were washed with brine, dried (MgSO4), filtered, and concentrated. Purification by reverse phase HPLC eluting with MeCN:H2O afforded the title compound as a white solid. LC-MS: calculated for C25H17ClN2O3 428.87, observed m/e 429.5 (M+H)+ (Rt 2.19 min). 1H NMR (500 MHz, CD3OD): δ 7.92-7.84 (m, 5H), 7.58-7.54 (m, 1H), 7.53 (s, 1H), 7.52-7.48 (m, 2H), 7.46-7.39 (m, 3H), 2.62 (s, 3H).

Workup

customit was partitioned between EtOAc and 2 M aqueous HCl
extractionThe aqueous phase was extracted with EtOAc
washThe combined organics were washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customPurification by reverse phase HPLC
washeluting with MeCN

Sources & evidence

ORD record: ord-36f115c59d204842af7046f05023b04b
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394969B2

Reaction notes

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