Formaldehyde → HCID 69266287, compound

HRID 1279486Notes

Reaction equation

HRID 1279486 reaction equation
[C:1]([BH3-])#[N:2].[Na+].C=O.N1C=CC(CN[C:15]2[CH:33]=[CH:32][CH:31]=[CH:30][C:16]=2[C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)=[O:18])=CC=1.F[C:35](F)(F)[C:36](O)=O>O1CCCC1>[N:19]1[CH:20]=[CH:21][C:36]([CH2:35][C:15]2[C:33]([NH:2][CH3:1])=[CH:32][CH:31]=[CH:30][C:16]=2[C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)=[O:18])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 5003444Sodium cyanoborohydrideHCID 63988832-[(4-Pyridinylmethyl)amino]-N-[3-(trifluoromethyl)phenyl]benzamide

Product 1

HCID 69266287HCID 69266287, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium cyanoborohydride (0.55 g, 14.1 mmol) is added to a stirred mixture of paraformaldehyde (0.82 g, 27.3 mmol) and 2-[(4-pyridyl)methyl]amino-N-[3-(trifluoromethyl)phenyl]benzamide (Example 14; 1.03 g, 2.78 mmol) in tetrahydrofuran (30 mL) at 20° C. under an argon atmosphere. The resulting mixture is then treated dropwise with trifluoroacetic acid (15 mL) and stirred at room temperature for 20 hours. The mixture diluted with ice-cold aqueous sodium hydroxide (100 mL of 5M) and extracted with dichloromethane (3×100 mL). The organic phase is dried (Na2SO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by column chromatography on silica gel, eluent ethyl acetate, to give the title compound as a colourless crystalline solid.

Workup

  1. extractionextracted with dichloromethane (3×100 mL)
  2. dry with materialThe organic phase is dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent is evaporated off under reduced pressure
  5. customto yield the crude product which
  6. customis purified by column chromatography on silica gel, eluent ethyl acetate

Sources & evidence

ORD record
ord-378acacabb4648d892c6f79d383e8b8f
Source dataset
uspto-grants-2002_09
Patent number
US06448277B2

Reaction notes

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