Sodium Hydroxide → HCID 58896464, compound

HRID 2235571Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:14][C:15]2[N:19]([CH3:20])[C:18]3[C:21]([N:25]([CH2:29][CH2:30][CH3:31])[CH2:26][CH2:27][CH3:28])=[CH:22][CH:23]=[CH:24][C:17]=3[N:16]=2)=[C:6]([CH:13]=1)[O:7]C(CC)C#N.[OH-:32].[Na+]>CCO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:14][C:15]2[N:19]([CH3:20])[C:18]3[C:21]([N:25]([CH2:26][CH2:27][CH3:28])[CH2:29][CH2:30][CH3:31])=[CH:22][CH:23]=[CH:24][C:17]=3[N:16]=2)=[C:6]([CH:13]=1)[O:7][CH2:3][CH2:4][CH2:5][C:6]([OH:7])=[O:32]

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 63 mg (0.14 mmol) of 4-[(5-chloro-2-[[7-(dipropylamino)-1-methyl-1H-benzimidazol-2-yl]amino]phenoxy]butanenitrile in 3 mL of EtOH and 1 mL of water was added 29 mg (0.72 mmol) of sodium hydroxide pellets and the reaction was stirred at 75° C. for 48 h. To the reaction mixture was added 75 mg (1.87 mmol) of sodium hydroxide pellets and the reaction heated at 75° C. for 24 h and concentrated in vacuo to a residue. The thus obtained residue was dissolved in 5 mL of water and the pH was adjusted to 4-5 using hydrochloric acid (1N aqueous solution). The resulting slurry was filtered, and the solids were washed with water and dried under high vacuum to give 46 mg (70%) of the title compound as white solids.

Workup

temperaturethe reaction heated at 75° C. for 24 h
concentrationconcentrated in vacuo to a residue
dissolutionThe thus obtained residue was dissolved in 5 mL of water
filtrationThe resulting slurry was filtered
washthe solids were washed with water
customdried under high vacuum

Sources & evidence

ORD record: ord-419721113e9449b2abae775147b6023c
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714009B2

Reaction notes

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