Trifluoroacetic acid → HCID 10023999, compound

HRID 1452651Notes

Reaction equation

HRID 1452651 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][C:35]=1[F:36])[NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([NH:13][C:14]1[CH:15]=[C:16]([CH:20]2[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]2)[CH:17]=[CH:18][CH:19]=1)=[O:12].FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][C:35]=1[F:36])[NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:15]=1)=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57526952HCID 57526952, compound

Product 1

HCID 10023999HCID 10023999, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a solution of tert-butyl 4-(3-{[6-(3,4-difluoroanilino)hexanoyl]amino}phenyl)-1-piperidine carboxylate (11.2 mg, 0.0224 mmol) in dichloromethane (0.500 mL) at 0° C. was slowly added trifluoroacetic acid (25.5 mg, 2.24 mmol). The reaction mixture was stirred at room temperature for 10 min and concentrated in vacuo. The residue was dissolved in i-PrOH/CHCl3 (1:3, 10 mL) and basified to pH 11 with 10% KOH, washed with H2O, followed by brine. The organic layer was dried over MgSO4 and concentrated in vacuo to give the desired product (8.98 mg, 99%): 1H NMR (400. MHz, CDCl3) δ 7.39-7.08 (m, 5H), 7.06-6.94 (m, 2H), 6.91-6.81 (m, 1H), 6.77-6.67 (m, 1H), 3.54-3.42 (m, 2H), 3.25-3.04 (m, 3H), 2.91-2.80 (m, 1H), 2.45-2.32 (m, 2H), 2.11-1.99 (m, 2H), 1.98-1.83 (m, 2H), 1.80-1.62 (m, 4H), 1.55-1.40 (m, 2H), 1.34-1.23 (m, 1H); ESMS m/e: 402.2 (M+H)+.

Workup

  1. customat 0° C.
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in i-PrOH/CHCl3 (1:3, 10 mL)
  4. washwashed with H2O
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4c467d23442146c18b0a79231fb74d32
Source dataset
uspto-grants-2009_01
Patent number
US07473698B2

Reaction notes

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