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

HRID 59123Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:11]=[C:10]([CH2:12][O:13][CH2:14][C:15]([F:18])([F:17])[F:16])[N:9]=[C:8]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[C:30]([CH3:32])[N:29]=[N:28][CH:27]=3)=[C:22]([O:33][CH3:34])[CH:21]=2)[N:7]=1)=[CH2:5])C.O.Cl.C(=O)(O)[O-].[Na+]>O1CCOCC1.[Cl-].[Na+].O>[CH3:34][O:33][C:22]1[CH:21]=[C:20]([NH:19][C:8]2[N:7]=[C:6]([C:4](=[O:3])[CH3:5])[CH:11]=[C:10]([CH2:12][O:13][CH2:14][C:15]([F:17])([F:16])[F:18])[N:9]=2)[CH:25]=[CH:24][C:23]=1[C:26]1[CH:31]=[C:30]([CH3:32])[N:29]=[N:28][CH:27]=1

Participants

Conditions

Temperature: 40 °C

Procedure

4-(1-Ethoxyvinyl)-N-(3-methoxy-4-(6-methylpyridazin-4-yl)phenyl)-6-((2,2,2-trifluoroethoxy)-methyl)pyrimidin-2-amine (65 mg, 0.14 mmol) was dissolved in dioxane (10 mL). Water (0.5 mL) and hydrochloric acid (conc., 0.035 mL, 0.41 mmol) were added. The mixture was heated at 40° C. for 20 min. Sodium bicarbonate (s, 0.5 g) and brine (2 mL) were added and mixture was stirred for 10 min. The mixture was extracted with EtOAC (×2). The organic phase was dried (sodium sulfate) and evaporated to give the title compound as a solid 60 mg (98%).

Workup

extractionThe mixture was extracted with EtOAC (×2)
dry with materialThe organic phase was dried (sodium sulfate)
customevaporated

Sources & evidence

ORD record: ord-e5b10567eaee484db5144be8f7d8f912
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09439904B2

Reaction notes

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