Trifluoroacetic anhydride → [4-(7-Chloro-1,3-benzodioxol-5-yl)-2-pyrimidin-2-yl-5-(trifluoromethyl)pyrazol-3-yl]imino-diisopropyl-lambda4-sulfane

HRID 705708Notes

Reaction equation

HRID 705708 reaction equation
[CH:1]([S:4]([CH:6]([CH3:8])[CH3:7])=O)([CH3:3])[CH3:2].FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Cl:22][C:23]1[C:28]2[O:29][CH2:30][O:31][C:27]=2[CH:26]=[C:25]([C:32]2[C:36]([C:37]([F:40])([F:39])[F:38])=[N:35][N:34]([C:41]3[N:46]=[CH:45][CH:44]=[CH:43][N:42]=3)[C:33]=2[NH2:47])[CH:24]=1>ClCCl.N>[Cl:22][C:23]1[C:28]2[O:29][CH2:30][O:31][C:27]=2[CH:26]=[C:25]([C:32]2[C:36]([C:37]([F:39])([F:40])[F:38])=[N:35][N:34]([C:41]3[N:46]=[CH:45][CH:44]=[CH:43][N:42]=3)[C:33]=2[N:47]=[S:4]([CH:6]([CH3:8])[CH3:7])[CH:1]([CH3:3])[CH3:2])[CH:24]=1

Participants

6

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 16645Isopropyl sulfoxideHCID 900100644-(7-Chloro-1,3-benzodioxol-5-yl)-2-pyrimidin-2-yl-5-(trifluoromethyl)pyrazol-3-amine

Product 1

HCID 117966763[4-(7-Chloro-1,3-benzodioxol-5-yl)-2-pyrimidin-2-yl-5-(trifluoromethyl)pyrazol-3-yl]imino-diisopropyl-lambda4-sulfaneYield 8%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of diisopropyl sulfoxide (0.75 g, 5.6 mmo) in dichloromethane at −60° C. under argon was added dropwise trifluoroacetic anhydride (1.18 g, 5.6 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 (0.97 g, 2.5 mmol) was added and the solution stirred at −60° C. for 1 h. The reaction was diluted with aqueous ammonia; the organic layer 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 (80 mg; 8%).

Workup

  1. stirringthe solution stirred at −60° C. for 1 h
  2. customthe organic layer 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-13a3deb56a6846cb8d3139178c491fdf
Source dataset
uspto-grants-2015_11
Patent number
US09174967B2

Reaction notes

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