Imidazole → HCID 11191571, compound

HRID 1724220Notes

Reaction equation

HRID 1724220 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:17]2[CH2:20][CH:19]([C@H:21]([C:26]3[CH:31]=[C:30](F)[CH:29]=[C:28]([F:33])[CH:27]=3)[C:22]([F:25])([CH3:24])[CH3:23])[CH2:18]2)[C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])=[CH:4][CH:3]=1.[NH:34]1[CH:38]=[CH:37][N:36]=[CH:35]1.C([O-])([O-])=O.[K+].[K+].CCOCC>CS(C)=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([N:17]2[CH2:18][CH:19]([C@H:21]([C:26]3[CH:31]=[C:30]([N:34]4[CH:38]=[CH:37][N:36]=[CH:35]4)[CH:29]=[C:28]([F:33])[CH:27]=3)[C:22]([F:25])([CH3:23])[CH3:24])[CH2:20]2)[C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 67065912HCID 67065912, compound

Product 1

HCID 11191571HCID 11191571, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 90 mg (0.192 mmole) of 3-((R)-(4-chlorophenyl){3-[(1R)-1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl}methyl)benzonitrile, 17 mg (0.25 mmole) of imidazole and 40 mg (0.288 mmole) of K2CO3 l in 1.5 mL DMSO was stirred at 150° C. in a microwave (with cooling). After 4 h, the mixture was poured into 30 mL of ether and 5 mL of water. The layers were separated and the aqueous layer was washed with three 10 mL portions of ether and the combined organic extracts were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography using 25% acetone-hexane to afford the title compound; Mass Spectrum: m/e=517 (M+1, 35Cl); 519 (M+1, 37Cl).

Workup

  1. customThe layers were separated
  2. washthe aqueous layer was washed with three 10 mL portions of ether
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-47c052a1a0734d85bf9c4d787c3b15b2
Source dataset
uspto-grants-2009_02
Patent number
US07485732B2

Reaction notes

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