Trifluoroacetic acid → HCID 67254378, compound

HRID 1509309Notes

Reaction equation

HRID 1509309 reaction equation
[CH:1]1([CH2:4][C:5]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4([NH:27]C(=O)OC(C)(C)C)[CH2:26][CH2:25][CH2:24]4)=[CH:19][CH:18]=3)=[N:15][C:8]3[O:9][CH2:10][C:11](=[O:14])[N:12]([CH3:13])[C:7]=3[CH:6]=2)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>ClCCl>[NH2:27][C:23]1([C:20]2[CH:21]=[CH:22][C:17]([C:16]3[C:5]([CH2:4][CH:1]4[CH2:2][CH2:3]4)=[CH:6][C:7]4[N:12]([CH3:13])[C:11](=[O:14])[CH2:10][O:9][C:8]=4[N:15]=3)=[CH:18][CH:19]=2)[CH2:24][CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86683671HCID 86683671, compound

Product 1

HCID 67254378HCID 67254378, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl (1-(4-(7-(cyclopropylmethyl)-1-methyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (0.5 mg, 1.79 μmol) was dissolved in dichloromethane (1 ml). TFA (0.5 ml) was added at room temperature and the reaction mixture was stirred for 30 seconds. The solution was immediately concentrated to dryness under reduced pressure. The residue was dissolved in diethyl ether (˜1 ml) and concentrated to dryness under reduced pressure. This was repeated three times. The residue was then slurred in diethyl ether (1 ml) and after settling the supernatant solvent was removed by pipette. This was repeated twice. The residue was then slurred in n-hexane (1 ml) and after settling the supernatant solvent was removed by pipette. This was repeated twice. The residue remaining solvent was dried to give the desired product as an off-white solid as the title compound (0.3 mg, 77% yield). LCMS (Method D) RT=0.77 min, M+1=364. 1H-NMR (500 MHz, CD3OD) δ 7.66-7.50 (4H, m), 7.47 (1H, s), 4.48 (2H, s), 4.15-4.09 (2H,m), 3.06 (3H, s), 2.75-2.65 (2H, m), 2.51-2.42 (2H, m), 2.28-2.20 (1H, m), 1.97-1.90 (1H, m), 1.76-1.71 (1H, m), 1.66-1.55 (2H, m), 1.38-1.31 (2H, m).

Workup

  1. concentrationThe solution was immediately concentrated to dryness under reduced pressure
  2. dissolutionThe residue was dissolved in diethyl ether (˜1 ml)
  3. concentrationconcentrated to dryness under reduced pressure
  4. customwas removed by pipette
  5. customwas removed by pipette
  6. customwas dried

Sources & evidence

ORD record
ord-787c2be736fd4f95986b09b81301505a
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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