N2-(4-Methoxy-benzyl)-6-trifluoromethyl-pyridine-2,3-diamine → 6-(Trifluoromethyl)pyridine-2,3-diamine

HRID 912901Notes

Reaction equation

HRID 912901 reaction equation
COC1C=CC(C[NH:8][C:9]2[C:14]([NH2:15])=[CH:13][CH:12]=[C:11]([C:16]([F:19])([F:18])[F:17])[N:10]=2)=CC=1.C(O)(C(F)(F)F)=O.C(Cl)Cl>CO>[F:19][C:16]([F:17])([F:18])[C:11]1[N:10]=[C:9]([NH2:8])[C:14]([NH2:15])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 11630767N2-(4-Methoxy-benzyl)-6-trifluoromethyl-pyridine-2,3-diamineHCID 21863450Trifluoroacetic acid methylene chloride

Product 1

HCID 116798986-(Trifluoromethyl)pyridine-2,3-diamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N2-(4-methoxy-benzyl)-6-trifluoromethyl-pyridine-2,3-diamine from step (a) above (220 mg, 0.7 mmol) in 1:1 TFA/DCM (4 mL) was stirred at room temperature for 90 min. The reaction mixture was concentrated to yield a gummy residue, which was dissolved in MeOH (2 mL) and purified by preparative HPLC (gradient 0.1% trifluoroacetic acid in acetonitrile) to give the title compound as an amorphous solid. MS (ESI, pos. ion) m/z: 178 (M+1)

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto yield a gummy residue, which
  3. custompurified by preparative HPLC (gradient 0.1% trifluoroacetic acid in acetonitrile)

Sources & evidence

ORD record
ord-aebcc8deb56546718b499f3f98c9e39f
Source dataset
uspto-grants-2011_09
Patent number
US08026241B2

Reaction notes

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