Sodium Hydroxide → HCID 71251340, compound

HRID 1055059Notes

Reaction equation

[CH:1]1([CH:5]([NH:11][C:12]2[C:17]([F:18])=[CH:16][N:15]=[C:14]([C:19]3[C:27]4[C:22](=[N:23][CH:24]=[C:25]([F:28])[CH:26]=4)[NH:21][CH:20]=3)[N:13]=2)[CH2:6][C:7]([O:9]C)=[O:8])[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C1COCC1.CO.[NH4+].[Cl-].CCOC(C)=O>[CH:1]1([CH:5]([NH:11][C:12]2[C:17]([F:18])=[CH:16][N:15]=[C:14]([C:19]3[C:27]4[C:22](=[N:23][CH:24]=[C:25]([F:28])[CH:26]=4)[NH:21][CH:20]=3)[N:13]=2)[CH2:6][C:7]([OH:9])=[O:8])[CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a racemic solution of methyl 3-cyclobutyl-3-((5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)amino)propanoate (0.042 g, 0.109 mmol) in THF (1.5 mL) and MeOH (0.5 mL) was added NaOH (0.300 mL of 2 M solution, 0.600 mmol) and the reaction mixture was warmed to 50° C. After stirring the reaction mixture for 1 hour, the mixture was diluted with aqueous saturated NH4Cl solution and EtOAc. The organic layer was dried (MgSO4), filtered and evaporated to dryness to afford 36 mg of the desired product that was used without further purification: 1H NMR (400 MHz, d6-DMSO) δ 12.26 (s, 2H), 8.55 (d, J=9.7 Hz, 1H), 8.19 (dd, J=45.1, 15.8 Hz, 3H), 7.48 (d, J=8.1 Hz, 1H), 4.79 (s, 1H), 2.58 (dd, J=20.6, 12.2 Hz, 2H), 1.85 (ddd, J=29.4, 26.5, 21.1 Hz, 7H); LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, RT=2.10 minutes (M+H) 374.02.

Workup

dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
customevaporated to dryness

Sources & evidence

ORD record: ord-28b432b390b5465eabf57aa2a248a561
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394302B2

Reaction notes

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