Trifluoroacetic acid → HCID 68178642, compound

HRID 1520928Notes

Reaction equation

HRID 1520928 reaction equation
C(OC([N:8]([CH:19]([C:24]1[CH:25]=[N:26][C:27]([N:30]2[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[N:31]2)=[CH:28][CH:29]=1)[CH2:20][CH:21]([CH3:23])[CH3:22])[C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][N:10]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:22][CH:21]([CH3:23])[CH2:20][CH:19]([NH:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][N:10]=1)[C:24]1[CH:25]=[N:26][C:27]([N:30]2[CH:34]=[C:33]([C:35]([F:36])([F:38])[F:37])[CH:32]=[N:31]2)=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68178641HCID 68178641, compound

Product 1

HCID 68178642HCID 68178642, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a 0° C. solution of (+/−)-methyl 6-(tert-butoxycarbonyl(3-methyl-1-(6-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)butyl)amino)nicotinate (110 mg, 4.7 mmol) in dichloromethane (20 mL) was added trifluoroacetic acid (10 mL). The solution was stirred at 20° C. for 2 h. The solvent was removed under reduced pressure. The residue was dissolved in dichloromethane (20 mL) and washed with water (20 mL). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated to give (+/−)-methyl 6-(3-methyl-1-(6-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)butylamino)nicotinate (800 mg) as a colorless solid. 1H NMR (400 MHz, CDCl3) δ 11.11 (d, J=4.0 Hz, 1H), 8.76 (s, 1H), 8.45 (d, J=1.6 Hz, 1H), 8.36 (d, J=1.6 Hz, 1H), 8.17 (d, J=9.2 Hz, 1H), 7.96 (d, J=8.4 Hz, 1H), 7.86-7.82 (m, 2H), 6.59 (d, J=9.6 Hz, 1H), 4.54-4.49 (m, 1H), 3.83 (s, 3H), 2.06-1.97 (m, 1H), 1.72-1.58 (m, 2H), 0.96 (d, J=6.4 Hz, 3H), 0.89 (d, J=6.4 Hz, 3H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane (20 mL)
  3. washwashed with water (20 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e51eb34d0e5e42a9a36d06a96c06cd07
Source dataset
uspto-grants-2015_07
Patent number
US09073871B2

Reaction notes

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