Hydrochloric Acid → HCID 86706867, compound

HRID 717887Notes

Reaction equation

HRID 717887 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:16]=[C:17]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[N:27]=2)[C:18]([O:20]C(C)(C)C)=[O:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].Cl>O1CCCC1.[Cl-].[Na+].O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:16]=[C:17]([CH:25]=[C:26]([C:28]([F:30])([F:31])[F:29])[N:27]=2)[C:18]([OH:20])=[O:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86706866HCID 86706866, compound

Product 1

HCID 86706867HCID 86706867, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

tert-Butyl 2-{[1-(tert-butoxycarbonyl)piperidin-4-yl]amino}-6-(trifluoromethyl)isonicotinate (3.4 g, 7.6 mmol, from Step 1) was treated with potassium hydroxide (3.4 g, 61 mmol) in tetrahydrofuran (50. mL). After 2 hours, the mixture was acidified to pH 2-3 by the addition of 1.0 N HCl. Brine (50 mL) was also added and the product was extracted with three 50 mL portions of chloroform. The extracts were dried over sodium sulfate, filtered and concentrated to afford product as a light yellow powder (2.8 g, 94%). LCMS (M+Na)+: 412.0.

Workup

  1. extractionthe product was extracted with three 50 mL portions of chloroform
  2. dry with materialThe extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-278422efad384200b4b799af3ca7c5c9
Source dataset
uspto-grants-2015_11
Patent number
US09193733B2

Reaction notes

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