Trifluoroacetic acid → [6-Amino-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

HRID 1517077Notes

Reaction equation

HRID 1517077 reaction equation
COC1C=CC(C[NH:8][C:9]2[N:14]=[C:13]([C:15]([N:17]3[CH2:22][CH2:21][CH:20]([N:23]4[CH2:27][CH2:26][CH2:25][CH2:24]4)[CH2:19][CH2:18]3)=[O:16])[C:12]([CH3:28])=[CH:11][C:10]=2[C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=2)=CC=1.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[NH2:8][C:9]1[N:14]=[C:13]([C:15]([N:17]2[CH2:22][CH2:21][CH:20]([N:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)[CH2:19][CH2:18]2)=[O:16])[C:12]([CH3:28])=[CH:11][C:10]=1[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 58016724[6-(4-Methoxy-benzylamino)-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

Product 1

HCID 44547360[6-Amino-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanoneYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.48 g (2.7 mmol) of [6-(4-methoxy-benzylamino)-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (example 6) in 75 ml of CH2Cl2 was added 12.2 ml=18.2 g (160 mmol) of trifluoroacetic acid and the reaction mixture was subsequently heated up to reflux. After two hours, it was poured into crashed ice, the pH was adjusted to 8-9 with sodium carbonate solution and it was extracted twice with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 98:2 to 3:1) to give 1.04 g (90%) of the title compound as light yellow foam. MS: 433.3 (MH+).

Workup

  1. temperaturethe reaction mixture was subsequently heated up
  2. temperatureto reflux
  3. additionit was poured
  4. extractionwas extracted twice with CH2Cl2
  5. washthe organic phases were washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 98:2 to 3:1)

Sources & evidence

ORD record
ord-97a75ecaca7c4b17b24031908e59bf2b
Source dataset
uspto-grants-2012_07
Patent number
US08227613B2

Reaction notes

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