Hydrochloric Acid → HCID 67182174, compound

HRID 2425559Notes

Reaction equation

HRID 2425559 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([F:10])([F:9])[F:8])=[C:5]([C@@H:11]([NH:13][S@@](C(C)(C)C)=O)[CH3:12])[CH:4]=[N:3]1.[ClH:20]>O1CCOCC1>[ClH:20].[ClH:20].[CH3:1][N:2]1[C:6]([C:7]([F:8])([F:9])[F:10])=[C:5]([C@@H:11]([NH2:13])[CH3:12])[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67184064HCID 67184064, compound

Product 1

HCID 67182174HCID 67182174, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(R)-N-((S)-1-(1-methyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)ethyl)-2-methylpropane-2-sulfinamide (0.66 g, 0.0022 mole) was dissolved in HCl in dioxane (4M, 12 ml) and the solution stirred at RT overnight under nitrogen. The solution was evaporated and the residue suspended in ether and the white solid filtered off under a blanket of nitrogen. Yield 420 mg, 71% (hygroscopic). 1H NMR (400 MHz CD30D) δ 7.73 (s, 1H) 4.67, 4.65, 4.63, 4.62 (q, 1H) 4.02 (s, 3H) 1.62, 1.60 (d, 3H). MS (ESI) m/z 194 (M+H)+ 177 (M+H—NH3)+. TLC CH2Cl2:MeOH:NH4OH 95:5:0.5 0.2 UV−ve KMnO4+ve. The free base was isolated using a SCX column eluting with methanol and then methanolic ammonia (1M) to release the amine. [α]D=−11.43° (c 5.25, CH3OH).

Workup

  1. customThe solution was evaporated
  2. filtrationthe white solid filtered off under a blanket of nitrogen
  3. customThe free base was isolated
  4. washeluting with methanol

Sources & evidence

ORD record
ord-4012825667d1454c9af989a8315d9049
Source dataset
uspto-grants-2011_06
Patent number
US07964732B2

Reaction notes

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