Hydrochloric Acid → HCID 118208899, compound

HRID 595291Notes

Reaction equation

HRID 595291 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([N:11]3[CH:15]=[C:14]([C:16]4[CH:17]=[C:18]([NH:23][C:24]5[N:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][N:25]=5)[CH:19]=[C:20]([CH3:22])[CH:21]=4)[CH:13]=[N:12]3)[CH2:7][CH2:6]2)[O:4]CC1.Cl>C1COCC1.CCOC(C)=O>[CH3:22][C:20]1[CH:21]=[C:16]([C:14]2[CH:13]=[N:12][N:11]([CH:8]3[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]3)[CH:15]=2)[CH:17]=[C:18]([NH:23][C:24]2[N:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][N:25]=2)[CH:19]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118208964HCID 118208964, compound

Product 1

HCID 118208899HCID 118208899, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-{3-[1-(1,4-dioxaspiro[4.5]dec-8-yl)-1H-pyrazol-4-yl]-5-methylphenyl}-4-(trifluoromethyl)pyrimidin-2-amine (62.4 mg, 0.14 mmol) was dissolved in THF (1 mL) and hydrochloric acid (0.45 mL, 2.72 mmol) was added. The reaction mixture was stirred at room temperature for two hours. The mixture was diluted with EtOAc, washed with saturated sodium bicarbonate, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (10-80% EtOAc/hexanes) to afford 4-[4-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-1-yl]cyclohexanone as a colorless foam. MS ESI calcd. for C21H21F3N5O [M+H]+ 416. found 416. 1H NMR (500 MHz, DMSO-d6) δ 10.11 (s, 1H), 8.80 (d, J=4.7 Hz, 1H), 8.17 (s, 1H), 7.82 (s, 1H), 7.80 (s, 1H), 7.35 (s, 1H), 7.27 (d, J=4.7 Hz, 1H), 7.08 (s, 1H), 4.77-4.68 (m, 1H), 2.61-2.48 (m, 4H), 2.35-2.17 (m, 4H), 2.22 (s, 3H).

Workup

  1. washwashed with saturated sodium bicarbonate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (10-80% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c3f99e3e5eb441b4a85ec3975c02e031
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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