2,2-Difluorocyclopropane-1-carboxylic acid → HCID 118023411, compound

HRID 929309Notes

Reaction equation

HRID 929309 reaction equation
[Cl:1][C:2]1[C:6]([N:7]([CH2:17][CH3:18])[C:8](=[O:16])[CH2:9][CH2:10][NH:11][CH2:12][CH:13]([F:15])[F:14])=[CH:5][N:4]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[N:3]=1.[F:25][C:26]1([F:32])[CH2:28][CH:27]1[C:29](O)=[O:30]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[C:6]([N:7]([CH2:17][CH3:18])[C:8](=[O:16])[CH2:9][CH2:10][N:11]([CH2:12][CH:13]([F:15])[F:14])[C:29]([CH:27]2[CH2:28][C:26]2([F:32])[F:25])=[O:30])=[CH:5][N:4]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[N:3]=1

Participants

5

Reactant 2

HCID 27828232,2-Difluorocyclopropane-1-carboxylic acidHCID 89884642HCID 89884642, compound2×

Product 1

HCID 118023411HCID 118023411, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-3-((2,2-difluoroethyl)amino)-N-ethylpropanamide (0.10 g, 0.28 mmol) in CH2Cl2 (2 mL) were added 2,2-difluoro cyclopropanecarboxylic acid (0.041 g, 0.34 mmol), DMAP (0.034 g, 0.28 mmol) and N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-3-((2,2-difluoroethyl)amino)-N-ethylpropanamide (0.10 g, 0.28 mmol), and the mixture stirred at room temperature for 2 hours. The mixture was diluted with CH2Cl2 and washed with saturated aqueous NH4Cl and brine, dried over MgSO4, and concentrated under reduced pressure to give pink oil. The residue oil was purified on silica gel eluting with MeOH/CH2Cl2 to give the title compound F34 as a colorless oil (0.079 g, 58%).

Workup

  1. washwashed with saturated aqueous NH4Cl and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customto give pink oil
  5. customThe residue oil was purified on silica gel eluting with MeOH/CH2Cl2

Sources & evidence

ORD record
ord-552148f75df5443686a8aa055cdbe63b
Source dataset
uspto-grants-2016_03
Patent number
US09295260B2

Reaction notes

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