Sodium Hydroxide → HCID 59267463, compound

HRID 1945287Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][C:32](=[O:35])[N:31]([CH3:36])[CH:30]=3)=[CH:25][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:24]=[CH:25][C:26]([C:29]3[CH:34]=[CH:33][C:32](=[O:35])[N:31]([CH3:36])[CH:30]=3)=[CH:27][CH:28]=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

Methyl 5-({6-chloro-5-[4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl]-1H-benzimidazol-2-yl}oxy)-2-methylbenzoate (43 mg, 0.086 mmol) was dissolved in MeOH (1.7 mL). Then 2.5 M aqueous NaOH (0.5 mL, 1.250 mmol) was added, and the reaction was stirred at 50° C. for 2 h. The reaction mixture was concentrated, and then partitioned between EtOAc and water. The aqueous phase was acidified to pH=1 with 2 N aqueous HCl and extracted with EtOAc. The combined organic extracts were dried (MgSO4), filtered and concentrated to give the desired product as an off-white solid. LC-MS: calculated for C27H20ClN3O4 485.11, observed m/e 486.25 (M+H)+ (Rt: 1.85 min). 1H NMR (500 MHz, C2D6OS): δ 8.20 (s, 1H), 7.90 (d, 1H), 7.80 (s, 1H), 7.65 (d, 2H), 7.55 (s, 1H), 7.45-7.50 (m, 3H), 7.41 (d, 1H), 7.35 (s, 1H), 6.5 (d, 1H), 3.5 (s, 3H). 2.55 (s, 3H).

Workup

concentrationThe reaction mixture was concentrated
custompartitioned between EtOAc and water
extractionextracted with EtOAc
dry with materialThe combined organic extracts were dried (MgSO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-ae9a2da7e6db4f99ae3d6620b5dae9f0
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394969B2

Reaction notes

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