Sodium Hydroxide → 3-Amino-N-(2-amino-3,3,3-trifluoro-2-methylpropyl)-6-methoxy-5-(trifluoromethyl)picolinamide

HRID 887846Notes

Reaction equation

HRID 887846 reaction equation
[NH2:1][C:2]1[C:3]([C:14]([NH:16][CH2:17][C:18]([NH:24]CC2C=CC(OC)=CC=2)([CH3:23])[C:19]([F:22])([F:21])[F:20])=[O:15])=[N:4][C:5]([O:12][CH3:13])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[OH-].[Na+]>C(O)(C(F)(F)F)=O>[NH2:1][C:2]1[C:3]([C:14]([NH:16][CH2:17][C:18]([NH2:24])([CH3:23])[C:19]([F:22])([F:20])[F:21])=[O:15])=[N:4][C:5]([O:12][CH3:13])=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 584423323-Amino-6-methoxy-N-(3,3,3-trifluoro-2-(4-methoxybenzylamino)-2-methylpropyl)-5-(trifluoromethyl)picolinamide

Product 1

HCID 584423583-Amino-N-(2-amino-3,3,3-trifluoro-2-methylpropyl)-6-methoxy-5-(trifluoromethyl)picolinamide

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture comprising 3-amino-6-methoxy-N-(3,3,3-trifluoro-2-(4-methoxybenzylamino)-2-methylpropyl)-5-(trifluoromethyl)picolinamide (Ex. 18) (0.9 g, 1.873 mmo) in TFA (50 ml) was heated to 50° C. for 2 h. After cooling to RT, the pH was adjusted to pH 12 using 2M NaOH. The product was extracted with DCM and the organic extract was washed with water, dried over MgSO4 and concentrated in vacuo. The crude product was loaded onto a SCX-2 cartridge eluting with MeOH followed by 2M NH3 in MeOH. The methanolic ammonia fractions were concentrated in vacuo and dried under vacuum to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.35 (1H, m), 7.67 (1H, s), 6.67 (2H, s), 3.93 (3H, s), 3.58 (1H, m), 3.40 (1H, m), 2.22 (2H, s), 1.14 (3H, s).

Workup

  1. extractionThe product was extracted with DCM
  2. extractionthe organic extract
  3. washwas washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. washeluting with MeOH
  7. concentrationThe methanolic ammonia fractions were concentrated in vacuo
  8. customdried under vacuum

Sources & evidence

ORD record
ord-e81d7844acc64abbb4b2121b8f9073c1
Source dataset
uspto-grants-2012_08
Patent number
US08247436B2

Reaction notes

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