Hydrochloric Acid → HCID 71144245, compound

HRID 509320Notes

Reaction equation

HRID 509320 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C@H:9]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)[NH:10][S@](C(C)(C)C)=O)=[N:5][CH:6]=[CH:7][CH:8]=1.Cl.O1CCOCC1.C([O-])(O)=O.[Na+]>CO.CCOC(C)=O.O>[CH3:1][O:2][C:3]1[C:4]([C@H:9]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:19][CH:18]=2)[NH2:10])=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 71165363HCID 71165363, compound

Product 1

HCID 71144245HCID 71144245, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)—N—((S)-(3-methoxypyridin-2-yl)(4-(trifluoromethyl)-phenyl)methyl)-2-methylpropane-2-sulfinamide (0.576 g, 1.491 mmol) in MeOH (6 mL) was treated with hydrochloric acid, 4.0 M solution in 1,4-dioxane (0.75 mL, 3.00 mmol) and stirred at rt for 2 h. The reaction was concentrated on the rotary evaporator resulting in a gummy residue which was taken up in EtOAc (100 mL), saturated aqueous NaHCO3 (50 mL), and H2O (25 mL). The resulting mixture was transferred to a separatory funnel and after vigorous extraction, the organic layer was separated, dried over anhydrous sodium sulfate, and concentrated to yield the product (S)-(3-methoxypyridin-2-yl)(4-(trifluoromethyl)-phenyl)methanamine as a light-brown oil which was used without further purification in the next step.

Workup

  1. concentrationThe reaction was concentrated on the rotary evaporator
  2. customresulting in a gummy residue which
  3. customThe resulting mixture was transferred to a separatory funnel
  4. extractionafter vigorous extraction
  5. customthe organic layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d189d0dce82344b4959d5e615c68a961
Source dataset
uspto-grants-2015_08
Patent number
US09096527B2

Reaction notes

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