Trifluoroacetic acid → HCID 178425134, compound

HRID 2208774Notes

Reaction equation

HRID 2208774 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:25](=[O:37])[NH:26][CH2:27][C:28]2[C:29](=[O:36])[NH:30][C:31]([CH3:35])=[CH:32][C:33]=2[CH3:34])[C:5]([CH3:24])=[C:6]([N:8]([CH3:23])[C@@H:9]2[CH2:14][CH2:13][C@H:12]([NH:15]C(=O)OC(C)(C)C)[CH2:11][CH2:10]2)[CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:15][C@@H:12]1[CH2:11][CH2:10][C@H:9]([N:8]([CH3:23])[C:6]2[C:5]([CH3:24])=[C:4]([CH:3]=[C:2]([Br:1])[CH:7]=2)[C:25]([NH:26][CH2:27][C:28]2[C:29](=[O:36])[NH:30][C:31]([CH3:35])=[CH:32][C:33]=2[CH3:34])=[O:37])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178425136HCID 178425136, compound

Product 1

HCID 178425134HCID 178425134, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of cis-tert-butyl (4-((5-bromo-3-(((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamoyl)-2-methylphenyl)(methyl)amino)cyclohexyl)carbamate (0.8 g, 1.39 mmol) in DCM (25 mL) was cooled to 0° C. and TFA (5 mL) was added to it. The reaction mixture was stirred at room temperature for 1 h. Upon completion, reaction was concentrated to dryness. Residue was basified with aqueous sodium bicarbonate till pH 8 and aqueous layer extracted with 20% MeOH/DCM. The combined organic layers were dried over sodium sulfate, filtered and concentrated to afford the desired compound (600 mg, 91% yield). LCMS: 475.15 (M+1)+; HPLC % 95.88 (@ 254 nm) (Rt; 4.832; Method: Column: YMC ODS-A 150 mm×4.6 mm×5μ; Mobile Phase: A; 0.05% TFA in water/B; 0.05% TFA in acetonitrile; Inj. Vol: 10 μL, Col. Temp.: 30° C.; Flow rate: 1.4 mL/min.; Gradient: 5% B to 95% B in 8 min, Hold for 1.5 min, 9.51-12 min 5% B); 1H NMR (DMSO-d6, 400 MHz) δ 8.22 (t, 1H), 7.20 (s, 1H), 7.01 (s, 1H), 5.85 (s, 1H), 4.23 (d, 2H, J=3.6 Hz), 2.82-2.86 (m, 2H), 2.53 (s, 3H), 2.18 (s, 3H), 2.13 (s, 3H), 2.10 (s, 3H), 1.82-1.84 (m, 2H), 1.34-1.44 (m, 6H).

Workup

  1. customUpon completion, reaction
  2. concentrationwas concentrated to dryness
  3. extractionextracted with 20% MeOH/DCM
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f32cd93d6c5c47d39b5052a22bb674ae
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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