Sodium Hydroxide → HCID 71251340, compound

HRID 2171856Notes

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-a0d4a2c704284a15aa81f24fe6f6772c
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051319B2

Reaction notes

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