Hydrochloric Acid → HCID 58257099, compound

HRID 2093793Notes

Reaction equation

[F:1][C:2]1[CH:8]=[C:7]([CH:9]2[CH2:18][CH2:17][C:12]3([O:16]CCO3)[CH2:11][CH2:10]2)[C:6]([CH3:19])=[CH:5][C:3]=1[NH2:4].Cl[C:21]1[N:26]=[C:25]([NH:27][C:28]2[CH:32]=[C:31]([CH3:33])[NH:30][N:29]=2)[C:24]([C:34]([F:37])([F:36])[F:35])=[CH:23][N:22]=1.Cl.CO>CC(O)C>[F:1][C:2]1[C:3]([NH:4][C:21]2[N:26]=[C:25]([NH:27][C:28]3[CH:32]=[C:31]([CH3:33])[NH:30][N:29]=3)[C:24]([C:34]([F:35])([F:37])[F:36])=[CH:23][N:22]=2)=[CH:5][C:6]([CH3:19])=[C:7]([CH:9]2[CH2:10][CH2:11][C:12](=[O:16])[CH2:17][CH2:18]2)[CH:8]=1

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of 2-fluoro-5-methyl-4-(1,4-dioxaspiro[4.5]decan-8-yl)aniline (318.6 mg, 1.2 mmol), 2-chloro-N-(5-methyl-1H-pyrazol-3-yl)-5-(trifluoromethyl)pyrimidin-4-amine (333.0 mg, 1.2 mmol) and HCl (4 N in water, 0.3 mL, 1.2 mmol) in i-PrOH (4.0 mL) was heated at 125° C. in an oil bath overnight. The reaction mixture was concentrated in vacuo. The resulting crude mixture was dissolved in THF (4 mL), MeOH (2 mL) and HCl (4N in water, 0.3 mL, 1.2 mmol), and stirred at room temperature for an additional 2 h. The reaction mixture was concentrated in vacuo, and purified by silica chromatography (0-100% EtOAC in hexanes gradient) to afford 4-(5-fluoro-2-methyl-4-(4-(5-methyl-1H-pyrazol-3-ylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)phenyl)cyclohexanone; ESMS m/z 463.2 (M+H+).

Workup

concentrationThe reaction mixture was concentrated in vacuo
dissolutionThe resulting crude mixture was dissolved in THF (4 mL)
concentrationThe reaction mixture was concentrated in vacuo
custompurified by silica chromatography (0-100% EtOAC in hexanes gradient)

Sources & evidence

ORD record: ord-d696c7fbf8ed45ba9d24538d80ae17be
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445505B2

Reaction notes

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