Hydrochloric Acid → 1-(6-(((3,3-Difluorocyclobutyl)methoxy)methyl)-2-(3-methoxy-4-(6-methylpyridazin-4-yl)phenylamino)pyrimidin-4-yl)ethanone

HRID 59083Notes

Reaction equation

[F:1][C:2]1([F:36])[CH2:5][CH:4]([CH2:6][O:7][CH2:8][C:9]2[CH:14]=[C:13]([C:15]([O:17]CC)=[CH2:16])[N:12]=[C:11]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[C:31]([CH3:33])[N:30]=[N:29][CH:28]=4)=[C:23]([O:34][CH3:35])[CH:22]=3)[N:10]=2)[CH2:3]1.O.Cl>O1CCOCC1>[F:36][C:2]1([F:1])[CH2:5][CH:4]([CH2:6][O:7][CH2:8][C:9]2[N:10]=[C:11]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[C:31]([CH3:33])[N:30]=[N:29][CH:28]=4)=[C:23]([O:34][CH3:35])[CH:22]=3)[N:12]=[C:13]([C:15](=[O:17])[CH3:16])[CH:14]=2)[CH2:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 4-(((3,3-difluorocyclobutyl)methoxy)methyl)-6-(1-ethoxyvinyl)-N-(3-methoxy-4-(6-methylpyridazin-4-yl)phenyl)pyrimidin-2-amine (104 mg, 0.21 mmol) in dioxane (15 mL) were added water (1 mL) and HCl (conc. 0.052 mL, 0.63 mmol). The mixture was stirred at 50° C. for 20 minutes. The solvent was evaporate and 50% saturated aqueous sodium bicarbonate solution was added. The mixture was extracted with DCM. The organic phase was separated on phase separator and evaporated to give the title compound (94 mg, 95%).

Workup

customThe solvent was evaporate
addition50% saturated aqueous sodium bicarbonate solution was added
extractionThe mixture was extracted with DCM
customThe organic phase was separated on phase separator
customevaporated

Sources & evidence

ORD record: ord-cb1099d71563439ca4db78dc61147e29
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09439904B2

Reaction notes

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