Phosphorus oxychloride → HCID 86721466, compound

HRID 869608Notes

Reaction equation

HRID 869608 reaction equation
[CH:1]1([C:4]2[N:5]=[C:6]3[C:11](O)=[N:10][CH:9]=[CH:8][N:7]3[C:13]=2[CH2:14][C:15]2[CH:34]=[CH:33][C:18]3/[C:19](=[C:29](/[CH3:32])\[C:30]#[N:31])/[C:20]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:21]=4[O:22][CH2:23][C:17]=3[CH:16]=2)[CH2:3][CH2:2]1.P(Cl)(Cl)([Cl:37])=O>>[Cl:37][C:11]1[C:6]2[N:7]([C:13]([CH2:14][C:15]3[CH:34]=[CH:33][C:18]4/[C:19](=[C:29](/[CH3:32])\[C:30]#[N:31])/[C:20]5[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:21]=5[O:22][CH2:23][C:17]=4[CH:16]=3)=[C:4]([CH:1]3[CH2:2][CH2:3]3)[N:5]=2)[CH:8]=[CH:9][N:10]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178456710HCID 178456710, compound

Product 1

HCID 86721466HCID 86721466, compoundYield 96%

Conditions

Temperature
110 °C

Procedure

[step 5] To (E)-2-{8-[(2-cyclopropyl-8-hydroxyimidazo[1,2-a]pyrazin-3-yl)methyl]-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrile (3.8 g, 8.3 mmol) obtained in step 4 was added phosphorus oxychloride (19 mL, 207 mmol), and the mixture was stirred with heating at 110° C. for 4 hr. The mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted 3 times with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give (E)-2-{8-[(8-chloro-2-cyclopropylimidazo[1,2-a]pyrazin-3-yl)methyl]-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrile (3.7 g, 96%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution
  2. additionwas added to the residue
  3. extractionthe mixture was extracted 3 times with ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-842e53d8ed2b48e399406d6abc981d99
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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