Water → HCID 10223326, compound

HRID 1007565Notes

Reaction equation

HRID 1007565 reaction equation
Cl[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][N:8]=2)[N:5]=[C:4]([CH:17]([F:19])[F:18])[C:3]=1[C:20]#[N:21].[CH3:22][C@H:23]1[O:28][C@@H:27]([CH3:29])[CH2:26][NH:25][CH2:24]1.[F-].[K+].O>CS(C)=O>[F:18][CH:17]([F:19])[C:4]1[C:3]([C:20]#[N:21])=[C:2]([N:25]2[CH2:24][C@H:23]([CH3:22])[O:28][C@H:27]([CH3:29])[CH2:26]2)[N:6]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][N:8]=2)[N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 522689Potassium FluorideHCID 6415002,6-Dimethylmorpholine, cis-HCID 12149009HCID 12149009, compound

Product 1

HCID 10223326HCID 10223326, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-Chloro-3-difluoromethyl-1-(5-methanesulfonyl-pyridin-2-yl)-1H-pyrazole-4-carbonitrile (1.24 g, 3.7 mmol) and 2,6-cis-dimethylmorpholine (0.86 g, 7.4 mmol) were dissolved in dry dimethylsulfoxide (DMSO) (13 ml) and potassium fluoride (0.43 g, 7.4 mmol) was added to the clear solution. The resulting mixture was stirred at 20° for a period of 2 hours. Analytical HPLC indicated the reaction completion. The reaction mixture was poured into water (50 ml) and the resulting mixture was extracted with ethyl acetate (30 ml). The organic extract was dried over sodium sulfate and concentrated with a rotary evaporator. The desired product (1.3 g, 85%) was isolated by triturating the residue with ether (10 ml) containing 3 drops of methanol, stirring the suspension overnight, filtering, and drying under high vacuum. MS: 412.5, r.t.: 2.2, 1HNMR: (in d6-DMSO solvent) 9.02(1H, d, J=2.4), 8.52(1H, dd, J=8.8, 2.8), 7.98(1H, d, J=8.8), 7.12(1H, t, J=52.8), 3.68(2H, m), 3.36(3H, s), 3.28(2H, m), 2.80(2H, m), 0.99 (6H, d, J=6.4) ppm, 13C-NMR: (in d6-DMSO solvent) 155.9, 154.2, 148.2, 139.6, 119.2, 113.2, 113.1, 112.0, 109.9, 79.0, 71.6, 55.9, 44.3, 18.9 ppm.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate (30 ml)
  2. extractionThe organic extract
  3. dry with materialwas dried over sodium sulfate
  4. concentrationconcentrated with a rotary evaporator

Sources & evidence

ORD record
ord-923fd6aa71c64f80ae362600c0dcccce
Source dataset
uspto-grants-2004_09
Patent number
US06794512B2

Reaction notes

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