Acetic Acid → HCID 57444455, compound

HRID 1911779Notes

Reaction equation

HRID 1911779 reaction equation
C1(CN(CC2CC2)[C:6]2[N:11]=[C:10]3[N:12]([CH3:16])[C:13]([CH3:15])=[N:14][C:9]3=C[C:7]=2C=O)CC1.FC(F)(F)C1C=C(C=C(C(F)(F)F)C=1)CN.C(O)(=[O:41])C.[BH3-]C#N.[Na+]>CO>[CH3:15][C:13]1[N:12]([CH3:16])[C:10]([NH:11][C:6](=[O:41])[CH3:7])=[CH:9][N:14]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5210993,5-Bis(trifluoromethyl)benzylamineHCID 5003444Sodium cyanoborohydrideHCID 58795813HCID 58795813, compound

Product 1

HCID 57444455HCID 57444455, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 5-(bis-cyclopropylmethyl-amino)-2,3-dimethyl-3H-imidazo[4,5-b]pyridine-6-carbaldehyde (0.220 g, 0.73 mmol.) and 3,5-bis-trifluoromethyl-benzylamine (215 mg, 0.87 mmol) in methanol (8 mL) was added acetic acid (0.042 mL, 0.073 mol) at 0° C. and the resulting reaction mixture was stirred for 15 min at the same temperature. NaCNBH3 (0.069 g, 0.011 mmol.) was added and the mixture was stirred at room temperature for 45 min. Methanol was removed under reduced pressure and the crude was extracted with ethyl acetate (250 mL) and washed with water (250 mL×2). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield 0.220 gof colorless gummy compound.

Workup

  1. customthe resulting reaction mixture
  2. stirringthe mixture was stirred at room temperature for 45 min
  3. customMethanol was removed under reduced pressure
  4. extractionthe crude was extracted with ethyl acetate (250 mL)
  5. washwashed with water (250 mL×2)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto yield 0.220 gof colorless gummy compound

Sources & evidence

ORD record
ord-10b30994bb5343af9e578cf4198ae426
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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