Triethylamine → (r)-2-[5-Amino-1-(2,2,2-trifluoro-ethyl)-1h-pyrazol-3-yl]-pyrrolidine-1-carboxylic acid benzyl ester

HRID 1034970Notes

Reaction equation

HRID 1034970 reaction equation
[C:1]([CH2:3][C:4]([C@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=O)#[N:2].Cl.[F:22][C:23]([F:28])([F:27])[CH2:24][NH:25][NH2:26].C(N(CC)CC)C>C(O)C>[CH2:14]([O:13][C:11]([N:7]1[CH2:8][CH2:9][CH2:10][C@@H:6]1[C:4]1[CH:3]=[C:1]([NH2:2])[N:25]([CH2:24][C:23]([F:28])([F:27])[F:22])[N:26]=1)=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21934076(2,2,2-Trifluoroethyl)hydrazinehydrochlorideHCID 131730883(R)-benzyl 2-(2-cyanoacetyl)pyrrolidine-1-carboxylate

Product 1

HCID 69179870(r)-2-[5-Amino-1-(2,2,2-trifluoro-ethyl)-1h-pyrazol-3-yl]-pyrrolidine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Example 69A (3.0 g, 11 mmol) in ethanol (10 mL) was added (2,2,2-Trifluoro-ethyl)-hydrazine HCl salt (2.3 g, 11 mmol) and triethylamine (1.84 mL, 13.2 mmol) at rt. The solution was heated under reflux for 4 h. After cooling, the reaction mixture was concentrated and the residue was separated by flash chromatography to give Example 69B. Yield: 3.5 g (88%). MS (DCI): m/z 369 (M+H)+.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 4 h
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated
  5. customthe residue was separated by flash chromatography
  6. customto give Example 69B

Sources & evidence

ORD record
ord-bcbd93061f7e4a7487b65e138fea5469
Source dataset
uspto-grants-2013_10
Patent number
US08546368B2

Reaction notes

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