Cyclopropanemethanamine → HCID 25141655, compound

HRID 508127Notes

Reaction equation

HRID 508127 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:30]([F:33])([F:32])[F:31])[O:13][N:12]=[C:11]([C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]([C:24]4[O:25][C:26](=[O:29])[CH2:27][N:28]=4)=[CH:16][CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH2:34][CH2:35][CH:36]1[CH2:38][CH2:37]1>CN(C)C=O.O>[CH:36]1([CH2:35][NH:34][C:26](=[O:29])[CH2:27][NH:28][C:24]([C:17]2[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:14]([C:11]3[CH2:10][C:9]([C:4]4[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=4)([C:30]([F:31])([F:33])[F:32])[O:13][N:12]=3)=[CH:15][CH:16]=2)=[O:25])[CH2:38][CH2:37]1

Participants

5

Reactant 2

HCID 75646CyclopropanemethanamineHCID 68513750HCID 68513750, compound2×

Product 1

HCID 25141655HCID 25141655, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-[4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenyl]-5(4H)-oxazolone (i.e. the title product of Step A) (50 mg) and (aminomethyl)cyclopropane (0.1 mL) in N,N-dimethylformamide (1 mL) was irradiated with microwave radiation to maintain a temperature around 150° C. for 30 minutes. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried with anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel using hexanes/ethyl acetate (3:2 to 3:7) as eluent to afford the title compound, a compound of the present invention, as a pale yellow solid (47 mg, 82% yield).

Workup

  1. customwas irradiated with microwave radiation
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-12b04e64387b4bcf9b6004729d9799d3
Source dataset
uspto-grants-2015_08
Patent number
US09095138B2

Reaction notes

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