Lithium Chloride → HCID 10163496, compound

HRID 1835306Notes

Reaction equation

HRID 1835306 reaction equation
C(OC(=O)[CH:5]([C:8]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[C:11]([C:21](=[O:39])[N:22]([CH2:24][C:25]2[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:26]=2)[CH3:23])=[CH:10][N:9]=1)[C:6]#[N:7])C.[Cl-].[Li+]>CS(C)=O>[F:37][C:35]([F:36])([F:38])[C:27]1[CH:26]=[C:25]([CH:30]=[C:29]([C:31]([F:34])([F:32])[F:33])[CH:28]=1)[CH2:24][N:22]([CH3:23])[C:21](=[O:39])[C:11]1[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])=[CH:13][C:8]([CH2:5][C:6]#[N:7])=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 433294Lithium ChlorideHCID 86584820HCID 86584820, compound

Product 1

HCID 10163496HCID 10163496, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 650 mg (1.15 mmol) (RS)-{5-[(3,5-bis-trifluoromethyl-benzyl)-methyl-carbamoyl]-4-o-tolyl-pyridin-2-yl}-cyano-acetic acid ethyl ester and 0.20 g (4.6 mmol) lithium chloride in wet dimethyl sulfoxide was stirred at 120° C. over night. After cooling the mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate and a saturated aqueous solution of sodium bicarbonate. The layers were separated and the aqueous layer was extracted with two portions of ethyl acetate. The combined organic extracts were washed with two portions of water, dried with magnesium sulfate and concentrated to give 595 mg of crude product. Flash chromatography afforded 396 mg (69.9%) of the title compound as a white solid.

Workup

  1. temperatureAfter cooling the mixture
  2. concentrationwas concentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with two portions of ethyl acetate
  6. washThe combined organic extracts were washed with two portions of water
  7. dry with materialdried with magnesium sulfate
  8. concentrationconcentrated
  9. customto give 595 mg of crude product

Sources & evidence

ORD record
ord-fbddbbed89ab4d93b47dc0cd13f265ac
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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