Methanesulfonic Acid → HCID 118208833, compound

HRID 595290Notes

Reaction equation

HRID 595290 reaction equation
[N-:1]=[N+]=[N-].[Na+].[O:5]1[C:9]2([CH2:14][CH2:13][CH:12]([N:15]3[CH:19]=[C:18]([C:20]4[CH:21]=[C:22]([NH:27][C:28]5[N:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][N:29]=5)[CH:23]=[C:24]([CH3:26])[CH:25]=4)[CH:17]=[N:16]3)[CH2:11][CH2:10]2)OCC1.CS(O)(=O)=O.[OH-].[Na+]>C(Cl)(Cl)Cl.O>[CH3:26][C:24]1[CH:25]=[C:20]([C:18]2[CH:17]=[N:16][N:15]([CH:12]3[CH2:11][CH2:10][NH:1][C:9](=[O:5])[CH2:14][CH2:13]3)[CH:19]=2)[CH:21]=[C:22]([NH:27][C:28]2[N:33]=[C:32]([C:34]([F:35])([F:36])[F:37])[CH:31]=[CH:30][N:29]=2)[CH:23]=1

Participants

7

Reactant 4

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 118208964HCID 118208964, compound

Product 1

HCID 118208833HCID 118208833, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
65 °C

Procedure

Sodium azide (155 mg, 2.39 mL) was added to a solution of N-{3-[1-(1,4-dioxaspiro[4.5]dec-8-yl)-1H-pyrazol-4-yl]-5-methylphenyl}-4-(trifluoromethyl)pyrimidin-2-amine (732 mg, 1.59 mmol) in chloroform (8.0 mL) followed by methanesulfonic acid (1.24 mL, 19.1 mmol). The reaction was heated to 65° C. for 2 h. The reaction was cooled to room temperature and water was added, followed by NaOH (1N). The organic layer was extracted with EtOAc (3×). The combined layers were dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (10% methanol/dichloromethane) to afford racemic 5-[4-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-1-yl]azepan-2-one as a white solid. MS ESI calcd. for C21H21F3N6O [M+H]+ 431. found 431.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionThe organic layer was extracted with EtOAc (3×)
  3. dry with materialThe combined layers were dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-cbb0fa43d1ba41ecacf508e097d47cfe
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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