Sodium Hydroxide → HCID 57378433, compound

HRID 72551Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:24]2[CH2:27][CH:26]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=3[F:36])[CH2:25]2)=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)=[O:8].[OH-].[Na+]>C1OCCOC1.O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:24]2[CH2:25][CH:26]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=3[F:36])[CH2:27]2)=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1([C:13]2[CH:22]=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)[CH2:11][CH2:12]1)=[O:8]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 4-(1-(5-chloro-2-(3-((2,4-difluorophenyl)amino)azetidin-1-yl)nicotinamido)cyclopropyl)benzoate (D169) (12 mg, 0.024 mmol) in a mixture 1-4 dioxane/water (3 ml/1 ml), 1N NaOH (0.036 ml) was added. The reaction mixture was stirred 12 h at 60° C. Organic solvent was evaporated in vacuo and the reaction mixture was acidified with 2N HCl (pH=2) and the resulting mixture was extracted with ethylacetate (3×5 ml). Combined organics were evaporated in vacuo and the residue was loaded on SNAP-C18 gold cartridge (15 g) eluting with H2O-AcOH (0.1%)/CH3CN—AcOH (0.1%) from 10/90 to 0/100. Collected fractions were evaporated in vacuo to afford the title (E35) (5 mg)

Workup

customOrganic solvent was evaporated in vacuo
extractionthe resulting mixture was extracted with ethylacetate (3×5 ml)
customCombined organics were evaporated in vacuo
washeluting with H2O-AcOH (0.1%)/CH3CN—AcOH (0.1%) from 10/90 to 0/100
customCollected fractions were evaporated in vacuo

Sources & evidence

ORD record: ord-a3aa66e2034d46b19ae03621b8e95d72
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08828987B2

Reaction notes

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