Lithium hydroxide, monohydrate → 3-((2-((2-Phenylpyrimidin-5-yl)carbamoyl)-4-(piperidin-1-yl)phenyl)carbamoyl)benzoic acid

HRID 926798Notes

Reaction equation

[C:1]1([C:7]2[N:12]=[CH:11][C:10]([NH:13][C:14]([C:16]3[CH:21]=[C:20]([N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)[CH:19]=[CH:18][C:17]=3[NH:28][C:29]([C:31]3[CH:32]=[C:33]([CH:38]=[CH:39][CH:40]=3)[C:34]([O:36]C)=[O:35])=[O:30])=[O:15])=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Li+]>O1CCCC1.O>[C:1]1([C:7]2[N:12]=[CH:11][C:10]([NH:13][C:14]([C:16]3[CH:21]=[C:20]([N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)[CH:19]=[CH:18][C:17]=3[NH:28][C:29]([C:31]3[CH:32]=[C:33]([CH:38]=[CH:39][CH:40]=3)[C:34]([OH:36])=[O:35])=[O:30])=[O:15])=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of methyl 3-((2-((2-phenylpyrimidin-5-yl)carbamoyl)-4-(piperidin-1-yl)phenyl)carbamoyl)benzoate (1200 mg, 2.02 mmol, 1.00 equiv, 90%) in tetrahydrofuran/water (5:1) (30 mL) was added lithium hydroxide hydrate (420 mg, 9.97 mmol, 8.00 equiv, 95%) and the resulting solution was stirred for 3 h at 40° C. in an oil bath. The mixture was concentrated under vacuum and the residue was adjusted to pH 3-4 with hydrochloric acid. The mixture was extracted with 3×100 mL of tetrahydrofuran and the organic layers combined, washed with 1×100 mL of brine and then concentrated under vacuum to afford 1000 mg (95%) of a green to yellow solid.

Workup

concentrationThe mixture was concentrated under vacuum
extractionThe mixture was extracted with 3×100 mL of tetrahydrofuran
washwashed with 1×100 mL of brine
concentrationconcentrated under vacuum
customto afford 1000 mg (95%) of a green to yellow solid

Sources & evidence

ORD record: ord-13102e623d914659b7aef58271c6c437
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09289429B2

Reaction notes

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