Trifluoroacetic acid → 5-nitro-N4-piperidin-4-ylmethyl-N2-(2-trifluoromethoxy-benzyl)-pyridine-2,4-diamine

HRID 2376708Notes

Reaction equation

HRID 2376708 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][N:19]=[C:18]([NH:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][C:34]([F:37])([F:36])[F:35])[CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N+:22]([C:21]1[C:16]([NH:15][CH2:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[CH:17][C:18]([NH:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][C:34]([F:37])([F:35])[F:36])=[N:19][CH:20]=1)([O-:24])=[O:23]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 587126844-{[5-Nitro-2-(2-trifluoromethoxy-benzylamino)-pyridin-4-ylamino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 119512495-nitro-N4-piperidin-4-ylmethyl-N2-(2-trifluoromethoxy-benzyl)-pyridine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-{[5-Nitro-2-(2-trifluoromethoxy-benzylamino)-pyridin-4-ylamino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester (91 mg, 0.17 mmol) was dissolved in CH2Cl2 (2.5 mL). TFA (2.5 mL) was added and the reaction was stirred for 3 h. The volatiles were removed and the resultant residue was redissolved in EtOAc and poured into 10% aqueous NaHCO3. The aqueous phase was separated and extracted two more times with EtOAc. The organic layers were combined, dried (Na2SO4), decanted and concentrated. The crude product was purified by SiO2 chromatography (1:10:89, NH4OH:CH3OH:CH2Cl2) to afford 5-nitro-N4-piperidin-4-ylmethyl-N2-(2-trifluoromethoxy-benzyl)-pyridine-2,4-diamine as a yellow solid, m/z 426.4 (M+H)+ (28 mg, 39%).

Workup

  1. customThe volatiles were removed
  2. dissolutionthe resultant residue was redissolved in EtOAc
  3. additionpoured into 10% aqueous NaHCO3
  4. customThe aqueous phase was separated
  5. extractionextracted two more times with EtOAc
  6. dry with materialdried (Na2SO4)
  7. customdecanted
  8. concentrationconcentrated
  9. customThe crude product was purified by SiO2 chromatography (1:10:89, NH4OH:CH3OH:CH2Cl2)

Sources & evidence

ORD record
ord-80edf0b41fb3424892e1c39ef7a9f3ca
Source dataset
uspto-grants-2008_12
Patent number
US07468382B2

Reaction notes

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