Sodium Hydroxide → HCID 178460698, compound

HRID 1525248Notes

Reaction equation

[OH:1][C:2]1[C:7]([C:8]([NH:10][CH:11]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:12]2[CH:17]=[CH:16][C:15]([P:18]([CH2:23][CH2:24][CH3:25])(=[O:22])[O:19]CC)=[CH:14][CH:13]=2)=[O:9])=[CH:6][N:5]=[C:4]([N:32]2[CH:36]=[CH:35][CH:34]=[N:33]2)[N:3]=1.[OH-].[Na+]>O1CCOCC1>[OH:1][C:2]1[C:7]([C:8]([NH:10][CH:11]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:12]2[CH:13]=[CH:14][C:15]([P:18]([CH2:23][CH2:24][CH3:25])(=[O:19])[OH:22])=[CH:16][CH:17]=2)=[O:9])=[CH:6][N:5]=[C:4]([N:32]2[CH:36]=[CH:35][CH:34]=[N:33]2)[N:3]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of ethyl 4-((4-hydroxy-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxamido)(phenyl)methyl)phenyl(propyl)phosphinate, 16-f, (2.1 g, 4.16 mmol) in dioxane (30 ml) was added 2N NaOH (0.83 g, 20.8 mmol). The mixture was stirred at 85° C. for 6-8 hours, then evaporated the solvent and the residue was added water (20 ml) and extracted with ethyl acetate (30 ml) twice. The aqueous phase was adjusted to pH=1˜2 with conc. HCl, then filtered, and the filtered solid was washed with water, dried to give the title compound, 16-1, (crude product), which was further purified by prep_HPLC to give pure 16-1 (400 mg). 1H NMR (300 MHz, DMSO-d6): δ 10.38 (s, 1H), 8.61 (d, 1H), 8.42 (s, 1H), 8.06 (s, 1H), 7.34 (m, 9H), 6.72 (s, 1H), 6.32 (d, 1H), 1.75 (m, 2H), 1.41 (m, 2H), 0.95 (t, 3H). (M+H)+=478.2.

Workup

customevaporated the solvent
additionthe residue was added water (20 ml)
extractionextracted with ethyl acetate (30 ml) twice
filtrationfiltered
washthe filtered solid was washed with water
customdried

Sources & evidence

ORD record: ord-f01fa0584a3d4f84b3d6072ea4ddb029
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079930B2

Reaction notes

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