Propargyl bromide → HCID 178460293, compound

HRID 216005Notes

Reaction equation

HRID 216005 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:7][C:8]1[CH:9]=[C:10]([C:15]2([C:31]([F:34])([F:33])[F:32])[O:19][N:18]=[C:17]([C:20]3[CH:29]=[CH:28][C:23]([C:24]([NH:26][OH:27])=[NH:25])=[C:22]([CH3:30])[CH:21]=3)[CH2:16]2)[CH:11]=[C:12]([Cl:14])[CH:13]=1.[CH2:35](Br)[C:36]#[CH:37]>CN(C)C=O.O>[Cl:7][C:8]1[CH:9]=[C:10]([C:15]2([C:31]([F:32])([F:34])[F:33])[O:19][N:18]=[C:17]([C:20]3[CH:29]=[CH:28][C:23]([C:24]([NH:26][O:27][CH2:37][C:36]#[CH:35])=[NH:25])=[C:22]([CH3:30])[CH:21]=3)[CH2:16]2)[CH:11]=[C:12]([Cl:14])[CH:13]=1

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 10796Cesium carbonateHCID 178423542HCID 178423542, compound

Product 1

HCID 178460293HCID 178460293, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Caesium carbonate (0.122 g) was added to a solution of 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-N-hydroxy-2-methyl-benzamidine (0.1 g) (Example P1) in N,N-dimethylformamide (8 ml). Propargyl bromide (80% w/v in toluene) (0.028 ml) was added. The reaction mixture was stirred at ambient temperature for 20 hours. The reaction mixture was diluted with water and the mixture extracted twice with ethyl acetate. The combined organic phases were washed with water, dried over sodium sulfate, and concentrated. The residue was purified by preparative HPLC to give Compound No. A2 of Table A (0.054 g) as a yellow oil.

Workup

  1. extractionthe mixture extracted twice with ethyl acetate
  2. washThe combined organic phases were washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC
  6. customto give Compound No

Sources & evidence

ORD record
ord-c18b696ee262414581d02adbbef39c6a
Source dataset
uspto-grants-2012_06
Patent number
US08193221B2

Reaction notes

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