Trifluoroacetic acid → HCID 70913262, compound

HRID 2208895Notes

Reaction equation

HRID 2208895 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:27](=[O:39])[NH:28][CH2:29][C:30]2[C:31](=[O:38])[NH:32][C:33]([CH3:37])=[CH:34][C:35]=2[CH3:36])[C:5]([CH2:25][CH3:26])=[C:6]([N:8]([CH2:23][CH3:24])[CH:9]2[CH2:14][CH2:13][CH:12]([NH:15]C(=O)OC(C)(C)C)[CH2:11][CH2:10]2)[CH:7]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:15][CH:12]1[CH2:11][CH2:10][CH:9]([N:8]([CH2:23][CH3:24])[C:6]2[C:5]([CH2:25][CH3:26])=[C:4]([CH:3]=[C:2]([Cl:1])[CH:7]=2)[C:27]([NH:28][CH2:29][C:30]2[C:31](=[O:38])[NH:32][C:33]([CH3:37])=[CH:34][C:35]=2[CH3:36])=[O:39])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70873918HCID 70873918, compound

Product 1

HCID 70913262HCID 70913262, compoundYield 130.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of tert-butyl N-{4-[(5-chloro-3-{[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]carbamoyl}-2-ethylphenyl)(ethyl)amino]cyclohexyl}carbamate (100 mg, 0.18 mmol) in CH2Cl2 (4.0 ml) at 0° C., was added trifluoroacetic acid (1.0 ml). The reaction mixture was stirred at 0° C. for 40 minutes and then stirred for 2 hours at room temperature. The reaction mixture was concentrated in-vacuo and the residue was basified with a saturated solution of NaHCO3 (aq) (10 ml) until the pH was 8. The aqueous residue was extracted with 20% MeOH/CH2Cl2 (4×15 ml). The combined organic layers were dried (MgSO4), filtered and concentrated in-vacuo to give the title compound (108 mg, 113%) as a yellow solid. LC-MS 48%, 2.88 min (7 minute LC-MS method), m/z=459.1 and 39%, 2.96 min (7 minute LC-MS method), m/z=459.1. 1H NMR shows a mixture of cis/trans isomers.

Workup

  1. stirringstirred for 2 hours at room temperature
  2. concentrationThe reaction mixture was concentrated in-vacuo
  3. extractionThe aqueous residue was extracted with 20% MeOH/CH2Cl2 (4×15 ml)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-74fbad2b356748278e813f58c0ce2257
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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