Water → HCID 86713532, compound

HRID 1847130Notes

Reaction equation

HRID 1847130 reaction equation
[CH3:1][C@H:2]1[O:7][C@H:6]([CH3:8])[CH2:5][NH:4][CH2:3]1.C(N(CC)CC)C.[F:16][C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([CH:26]=[O:27])[C:24]=1F)[C:20]#[N:21].O>C(#N)C>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:24]2[C:23]([CH:26]=[O:27])=[CH:22][C:19]([C:20]#[N:21])=[CH:18][C:17]=2[F:16])[CH2:5][C@@H:6]([CH3:8])[O:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 11137133trans-2,6-DimethylmorpholineHCID 230702283,4-Difluoro-5-formylbenzonitrile

Product 1

HCID 86713532HCID 86713532, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

(2R,6R)-2,6-dimethylmorpholine (8.0 g, 70.0 mmol) followed by triethylamine (13.7 mL, 98.0 mmol) is added slowly to a solution of commercially available 3,4-difluoro-5-formylbenzonitrile (11.1 g, 66.7 mmol) in acetonitrile (500 mL) at room temperature. The mixture is warmed to 80° C. for 16 hours. After allowing to cool to room temperature, water (500 mL) is added and the mixture extracted twice with ethylacetate (250 mL). The combined organics were washed with brine, dried over sodium sulfate, filtered and evaporated to give the title compound (18.1 g): LCMS (M+H) 262.3.

Workup

  1. temperatureto cool to room temperature
  2. extractionthe mixture extracted twice with ethylacetate (250 mL)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-dd18e556e3654a27a935d9df282859e7
Source dataset
uspto-grants-2015_02
Patent number
US08952149B2

Reaction notes

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