Sodium Hydroxide → HCID 66779140, compound

HRID 2091410Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:11]=[CH:12][C:13]3[O:17][C:16]([CH:18]([NH:25][C:26]4[CH:31]=[CH:30][C:29]([C:32]([N:34]([CH3:42])[CH2:35][CH2:36][C:37]([O:39]CC)=[O:38])=[O:33])=[CH:28][CH:27]=4)[CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)=[C:15]([CH3:43])[C:14]=3[CH:44]=2)=[N:7][CH:8]=1)#[N:2].[OH-].[Na+]>O1CCCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:11]=[CH:12][C:13]3[O:17][C:16]([CH:18]([NH:25][C:26]4[CH:27]=[CH:28][C:29]([C:32]([N:34]([CH3:42])[CH2:35][CH2:36][C:37]([OH:39])=[O:38])=[O:33])=[CH:30][CH:31]=4)[CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)=[C:15]([CH3:43])[C:14]=3[CH:44]=2)=[N:7][CH:8]=1)#[N:2]

Participants

Conditions

Temperature: 50 °C

Procedure

Ethyl 3-{[(4-{[{5-[(5-cyanopyridin-2-yl)oxy]-3-methyl-1-benzofuran-2-yl}(cyclohexyl)methyl]amino}phenyl)carbonyl](methyl)amino}-propanoate (300 mg) obtained in Example A201 was dissolved in tetrahydrofuran (4.0 mL), and 1N aqueous sodium hydroxide solution (1.1 mL) was added to the solution, and the mixture was stirred at 50° C. for 1 hr. The solvent was evaporated under reduced pressure, water (4 mL) was added to the residue, and the mixture was neutralized with 1N hydrochloric acid (1.1 mL) under ice-cooling and stirred at 0° C. for 30 min. The resulting precipitate was collected by filtration, and dried to give the title compound (271 mg, 87%) as a colorless amorphous form.

Workup

customThe solvent was evaporated under reduced pressure, water (4 mL)
additionwas added to the residue
temperaturecooling
stirringstirred at 0° C. for 30 min
filtrationThe resulting precipitate was collected by filtration
customdried

Sources & evidence

ORD record: ord-f26b7598bd6e4193bd6b3b291fadb1b1
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436043B2

Reaction notes

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