Dimethyl Sulfoxide → HCID 86717887, compound

HRID 1844139Notes

Reaction equation

HRID 1844139 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([NH2:12])=[N:8][CH:9]=[CH:10][CH:11]=1.Cl[CH:19]([C:25]([CH:27]1[CH2:29][CH2:28]1)=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21].CS(C)=O.O>C(O)C.CO>[CH:27]1([C:25]2[N:12]=[C:7]3[C:6]([O:5][CH2:4][C:3]4[C:13]([F:17])=[CH:14][CH:15]=[CH:16][C:2]=4[F:1])=[CH:11][CH:10]=[CH:9][N:8]3[C:19]=2[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:29][CH2:28]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 102634983-(2,6-Difluoro-benzyloxy)-pyridin-2-ylamineHCID 542445011033707-26-42×

Product 1

HCID 86717887HCID 86717887, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

1.69 g of 3-[(2,6-difluorobenzyl)oxy]pyridine-2-amine (Example 4A; 7.13 mmol, 1 equivalent) were initially charged in 44.4 ml of ethanol, and 425 mg of powdered molecular sieve 3 Å and 6.8 g of ethyl 2-chloro-3-cyclopropyl-3-oxopropanoate (crude product from Example 26A) were added. The resulting reaction mixture was heated at reflux for 48 h and then concentrated, and the residue was chromatographed (cyclohexane/ethyl acetate as mobile phase). The product-containing fractions were combined and concentrated under reduced pressure. The residue obtained in this manner was taken up in methanol, dimethyl sulphoxide and water and the solid formed was filtered off and dried under high vacuum. This gave 410 mg (15.4% of theory) of the title compound.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for 48 h
  4. concentrationconcentrated
  5. customthe residue was chromatographed (cyclohexane/ethyl acetate as mobile phase)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained in this manner
  8. filtrationwas filtered off
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-ad8af143d26f4d24bbf340b57063b882
Source dataset
uspto-grants-2015_02
Patent number
US08946215B2

Reaction notes

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