Hydrochloric Acid → N-(3-{6-[amino(dicyclopropyl)methyl]pyridin-3-yl}-5-methylphenyl)-4-(trifluoromethyl)pyrimidin-2-amine

HRID 2207412Notes

Reaction equation

HRID 2207412 reaction equation
CO.Cl.[CH:4]1([C:7]([CH:39]2[CH2:41][CH2:40]2)([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[C:25]([NH:27][C:28]4[N:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][N:29]=4)[CH:24]=[C:23]([CH3:38])[CH:22]=3)=[CH:17][N:16]=2)[NH:8][S@@](C(C)(C)C)=O)[CH2:6][CH2:5]1>O1CCOCC1.C([O-])(O)=O.[Na+]>[NH2:8][C:7]([CH:39]1[CH2:41][CH2:40]1)([CH:4]1[CH2:6][CH2:5]1)[C:15]1[N:16]=[CH:17][C:18]([C:21]2[CH:26]=[C:25]([NH:27][C:28]3[N:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][N:29]=3)[CH:24]=[C:23]([CH3:38])[CH:22]=2)=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 131735914(R)-N-{dicyclopropyl[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]methyl}-2-methylpropane-2-sulfinamide

Product 1

HCID 118092744N-(3-{6-[amino(dicyclopropyl)methyl]pyridin-3-yl}-5-methylphenyl)-4-(trifluoromethyl)pyrimidin-2-amine

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Methanol (5.00 mL) and HCl (4 M in dioxanes, 0.584 mL, 2.34 mmol) were added to (R)—N-{dicyclopropyl[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]methyl}-2-methylpropane-2-sulfinamide (317.5 mg, 0.584 mmol) and the reaction mixture was stirred for 25 minutes at room temperature. An additional 150 uL of 4 M HCl in dioxane was added to the reaction mixture, stirred for 45 minutes, diluted with saturated aqueous NaHCO3 (20.0 mL) and extracted with ethyl acetate (30.0 mL). The organic layer was washed with brine, dried over sodium sulfate, filtered, and was concentrated under reduced pressure to yield N-(3-{6-[amino(dicyclopropyl)methyl]pyridin-3-yl}-5-methylphenyl)-4-(trifluoromethyl)pyrimidin-2-amine. MS APCI calc'd for C24H25F3N5 [M+H]+ 440. found 440.

Workup

  1. stirringstirred for 45 minutes
  2. extractionextracted with ethyl acetate (30.0 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-1d92722aa77d41be861598d8b547870b
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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