Trifluoroacetic acid → HCID 58870681, compound

HRID 1927623Notes

Reaction equation

HRID 1927623 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[O:21])=[CH:16][C:15]=2[F:27])[CH2:10][CH2:9]1)=O)(C)(C)C.F[C:29](F)(F)[C:30]([OH:32])=O>C(Cl)Cl>[CH:22]1([C:20]([C:17]2[CH:18]=[CH:19][C:14]([N:11]3[CH2:12][CH2:13][N:8]([CH:29]([C:19]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:30]([N:8]([CH2:13][CH3:12])[CH2:9][CH3:10])=[O:32])[CH2:9][CH2:10]3)=[C:15]([F:27])[CH:16]=2)=[O:21])[CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69303640HCID 69303640, compound

Product 1

HCID 58870681HCID 58870681, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(4-cyclopentanecarbonyl-2-fluoro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (0.11 g, 0.29 mmol) in DCM (5 mL) was treated with trifluoroacetic acid (1.5 mL). After 3 h the solvent was removed and water (5 mL) and 1 M NaOH were added (˜pH 10). The mixture was extracted with DCM and the solvent removed. The residue was then taken up in DMF (2 mL) and K2CO3 was added (0.13 g, 0.91 mmol). This mixture was then treated with 2-bromo-N,N-diethyl-2-phenyl-acetamide (0.11 g) as described in previous examples to provide 0.072 g of the title compound. MS: 466.6. 1H NMR (CDCl3): 7.69-7.66 (m, 1H), 7.63-7.59 (m, 1H), 7.47-7.43 (m, 2H), 7.38-7.30 (m, 3H), 6.90-6.86 (m, 1H), 4.26 (s, 1H), 3.63-3.56 (m, 1H), 3.51-3.35 (m, 2H), 3.31-3.14 (m, 6H), 2.76-2.67 (m, 4H), 1.92-1.85 (m, 4H), 1.75-1.57 (m, 4H), 1.09 (t, J=7.1, 3H) 1.04 (t, J=7.1, 3H).

Workup

  1. customAfter 3 h the solvent was removed
  2. additionwater (5 mL) and 1 M NaOH were added (˜pH 10)
  3. extractionThe mixture was extracted with DCM
  4. customthe solvent removed
  5. additionK2CO3 was added (0.13 g, 0.91 mmol)
  6. additionThis mixture was then treated with 2-bromo-N,N-diethyl-2-phenyl-acetamide (0.11 g)

Sources & evidence

ORD record
ord-26aae4d98ace46c4892efd20a29cdf88
Source dataset
uspto-grants-2012_05
Patent number
US08183239B2

Reaction notes

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