Diethyl sulfoxide → [4-(7-Chloro-1,3-benzodioxol-5-yl)-2-pyrimidin-2-yl-5-(trifluoromethyl)pyrazol-3-yl]imino-diethyl-lambda4-sulfane

HRID 705707Notes

Reaction equation

HRID 705707 reaction equation
[CH2:1]([S:3]([CH2:5][CH3:6])=O)[CH3:2].FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Cl:20][C:21]1[C:26]2[O:27][CH2:28][O:29][C:25]=2[CH:24]=[C:23]([C:30]2[C:34]([C:35]([F:38])([F:37])[F:36])=[N:33][N:32]([C:39]3[N:44]=[CH:43][CH:42]=[CH:41][N:40]=3)[C:31]=2[NH2:45])[CH:22]=1>ClCCl.N>[Cl:20][C:21]1[C:26]2[O:27][CH2:28][O:29][C:25]=2[CH:24]=[C:23]([C:30]2[C:34]([C:35]([F:37])([F:38])[F:36])=[N:33][N:32]([C:39]3[N:44]=[CH:43][CH:42]=[CH:41][N:40]=3)[C:31]=2[N:45]=[S:3]([CH2:5][CH3:6])[CH2:1][CH3:2])[CH:22]=1

Participants

6

Reactant 3

HCID 6263Diethyl sulfoxideHCID 9845Trifluoroacetic anhydrideHCID 900100644-(7-Chloro-1,3-benzodioxol-5-yl)-2-pyrimidin-2-yl-5-(trifluoromethyl)pyrazol-3-amine

Product 1

HCID 117966776[4-(7-Chloro-1,3-benzodioxol-5-yl)-2-pyrimidin-2-yl-5-(trifluoromethyl)pyrazol-3-yl]imino-diethyl-lambda4-sulfaneYield 29%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of diethyl sulfoxide (0.47 g, 4.4 mmo) in dichloromethane at −60° C. under argon was added drop-wise trifluoroacetic anhydride (0.93 g, 4.4 mmol). The solution was stirred for 20 min at this temperature. Then the 4-(7-chloro-1,3-benzodioxol-5-yl)-2-pyrimidin-2-yl-5-(trifluoromethyl)pyrazol-3-amine (0.76 g, 2 mmol) was added and the solution stirred at −60 C for 1 h. The reaction was diluted with aqueous ammonia; the organic layer was separated and further washed with water and then dried and concentrated. The residue was re-crystallized with a mixture of ethyl acetate and petrole ether to give the title compound (270 mg; 29%).

Workup

  1. stirringthe solution stirred at −60 C for 1 h
  2. customthe organic layer was separated
  3. washfurther washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was re-crystallized with a mixture of ethyl acetate and petrole ether

Sources & evidence

ORD record
ord-f481bfcb1b0c4f7abd07007b7082c60c
Source dataset
uspto-grants-2015_11
Patent number
US09174967B2

Reaction notes

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