Trifluoroacetic acid → HCID 86708263, compound

HRID 534215Notes

Reaction equation

HRID 534215 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]([N:5]([CH2:21][CH:22]1[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]1)[C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=2)=[CH:11][CH:10]=1)=[O:4].C(O)(C(F)(F)F)=O>ClCCl>[F:35][C:2]([F:1])([F:36])[C:3]([N:5]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=2)=[CH:11][CH:10]=1)[CH2:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86708261HCID 86708261, compound

Product 1

HCID 86708263HCID 86708263, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-((2,2,2-trifluoro-N-(trans-2-(4-(1-methyl-1H-pyrazol-4-yl)phenyl)cyclopropyl)acetamido)methyl)piperidine-1-carboxylate (110 mg, 0.217 mmol) in dichloromethane (DCM) (2 mL) was added TFA (0.5 mL, 6.49 mmol), and the mixture was stirred at room temperature for 3 h. The mixture was concentrated and the residue was treated with saturated NaHCO3 aqueous solution and extracted with DCM (3×). The extract was dried (Na2SO4) and concentrated to give 85 mg of product as pale yellow solid. MS: (M+H)+=407.2. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.41-1.54 (m, 2H), 1.58-1.81 (m, 3H), 2.40-2.52 (m, 1H), 2.56-2.69 (m, 2H), 3.06-3.20 (m, 3H), 3.44-3.62 (m, 2H), 3.92-3.97 (m, 3H), 7.13 (d, J=8.34 Hz, 2H), 7.47-7.52 (m, 2H), 7.77-7.82 (m, 1H), 7.92-7.96 (m, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was treated with saturated NaHCO3 aqueous solution
  3. extractionextracted with DCM (3×)
  4. dry with materialThe extract was dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cd675e1c5edb4c7c9930b24255d55407
Source dataset
uspto-grants-2014_10
Patent number
US08853408B2

Reaction notes

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