Trifluoroacetic acid → HCID 57526951, compound

HRID 1452661Notes

Reaction equation

HRID 1452661 reaction equation
[O:1]([C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[CH:12]=2)[N:9]([C:19]([NH:21][CH2:22][CH2:23][CH2:24][C:25]([NH:27][C:28]2[CH:29]=[C:30]([CH:34]3[CH2:39][CH2:38][N:37](C(OC(C)(C)C)=O)[CH2:36][CH2:35]3)[CH:31]=[CH:32][CH:33]=2)=[O:26])=[O:20])[C:8](=[O:47])[NH:7][C:6]=1[CH3:48])=[O:4])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[O:1]([C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[CH:12]=2)[N:9]([C:19]([NH:21][CH2:22][CH2:23][CH2:24][C:25](=[O:26])[NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([CH:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)[CH:29]=2)=[O:20])[C:8](=[O:47])[NH:7][C:6]=1[CH3:48])=[O:4])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57526938HCID 57526938, compound

Product 1

HCID 57526951HCID 57526951, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a solution of tert-butyl 4-{3-[(4-{[(5-Methoxylcarbonyl-6-(3,4-difluorophenyl)-4-methyl-2-oxo-3,6-dihydro-1(2H)-pyrimidinyl)carbonyl]amino}butanoyl)amino]phenyl}-1-piperidinecarboxylate (378 mg, 0.579 mmol) in dichloromethane (5.00 mL) at 0° C. was slowly added trifluoroacetic acid (659 mg, 5.79 mmol). The reaction mixture was stirred at room temperature for 10 min and concentrated in vacuo. The residue was dissolved in iso-PrOH/CHCl3 (1:3, 10 mL) and basified to pH 11 with 10% KOH solution, washed with H2O, followed by brine. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (dichloromethane:methanol 5:1) to afford the desired product (93.8 mg, 29.3%): 1H NMR (400 MHz, CDCl3) δ 7.46-7.43 (m, 3H), 7.35-7.29 (m, 2H), 7.12-7.06 (m, 3H), 6.63-6.60 (m, 1H), 6.56-6.52 (m, 2H), 3.26 (s, 3H), 3.22 (s, 3H), 2.72 (dt, 6H, J=2.3, 12.3 Hz), 2.66 (tt, 2H, J=3.6, 11.9 Hz), 2.55 (tt, 1H, J=3.8, 11.9 Hz), 1.88-1.82 (m, 1H), 1.75-1.63 (m, 6H); ESMS m/e: 554.3 (M+H)+.

Workup

  1. customat 0° C.
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in iso-PrOH/CHCl3 (1:3, 10 mL)
  4. washwashed with H2O
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (dichloromethane:methanol 5:1)

Sources & evidence

ORD record
ord-091b6892485b4af49207470778704cda
Source dataset
uspto-grants-2009_01
Patent number
US07473698B2

Reaction notes

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