Trifluoroacetic acid → HCID 178495719, compound

HRID 548731Notes

Reaction equation

HRID 548731 reaction equation
FC(F)(F)C(O)=O.[CH3:8][C@H:9]([O:13][C:14]1[CH:15]=[C:16]([C:33]([NH:35][C:36]2[CH:40]=[CH:39][N:38](C(OC(C)(C)C)=O)[N:37]=2)=[O:34])[CH:17]=[C:18]([O:20][C:21]2[CH:32]=[CH:31][C:24]3[C:25](=[O:30])[N:26]([CH3:29])[CH2:27][O:28][C:23]=3[CH:22]=2)[CH:19]=1)[CH2:10][O:11][CH3:12]>C(Cl)Cl>[CH3:8][C@H:9]([O:13][C:14]1[CH:15]=[C:16]([CH:17]=[C:18]([O:20][C:21]2[CH:32]=[CH:31][C:24]3[C:25](=[O:30])[N:26]([CH3:29])[CH2:27][O:28][C:23]=3[CH:22]=2)[CH:19]=1)[C:33]([NH:35][C:36]1[CH:40]=[CH:39][NH:38][N:37]=1)=[O:34])[CH2:10][O:11][CH3:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 576632111,1-dimethylethyl 3-[({3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-5-[(3-methyl-4-oxo-3,4-dihydro-2H-1,3-benzoxazin-7-yl)oxy]phenyl}carbonyl)amino]-1H-pyrazole-1-carboxylate

Product 1

HCID 178495719HCID 178495719, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 mL) was added to a solution of 1,1-dimethylethyl 3-[({3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-5-[(3-methyl-4-oxo-3,4-dihydro-2H-1,3-benzoxazin-7-yl)oxy]phenyl}carbonyl)amino]-1H-pyrazole-1-carboxylate (190 mg, 0.34 mmol) in DCM (12 mL) and stirred at RT for 2 hours. The solvent was removed in vacuo and DCM (20 mL) added and the mixture washed with water (20 mL), saturated sodium bicarbonate solution (20 mL), brine (20 mL), dried (MgSO4), and reduced in vacuo to give the desired compound as a white solid (54 mg). 1H NMR δ (CDCl3): 1.32 (d, 3H), 3.09 (s, 3H), 3.40 (s, 3H), 3.47-3.63 (m, 2H), 4.56-4.63 (m, 1H), 5.16 (s, 2H), 6.52 (d, 1H), 6.71-6.74 (m, 1H), 6.81 (t, 1H), 6.85 (s, 1H), 7.18 (s, 1H), 7.37 (s, 1H), 7.49 (s, 1H), 7.92 (d, 1H), 9.46 (s, 1H), 9.46 (s, 1H); m/z 453 (M+H)+

Workup

  1. customThe solvent was removed in vacuo and DCM (20 mL)
  2. additionadded
  3. washthe mixture washed with water (20 mL), saturated sodium bicarbonate solution (20 mL), brine (20 mL)
  4. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-dd99e71d57e9410596c6da689e276d29
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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