Tetramethylene sulfoxide → HCID 90009949, compound

HRID 705709

Reaction equation

HRID 705709 reaction equation
[S:1]1(=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.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:38])([F:36])[F:37])=[N:33][N:32]([C:39]3[N:44]=[CH:43][CH:42]=[CH:41][N:40]=3)[C:31]=2[N:45]=[S:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:22]=1

Participants

6

Reactant 3

HCID 1128Tetramethylene sulfoxideHCID 9845Trifluoroacetic anhydrideHCID 900100644-(7-Chloro-1,3-benzodioxol-5-yl)-2-pyrimidin-2-yl-5-(trifluoromethyl)pyrazol-3-amine

Product 1

HCID 90009949HCID 90009949, compound

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.2 equivalents of tetrahydro-thiophene 1-oxide (0.23 g, 2.2 mmo) in dichloromethane at −60° C. under argon was added dropwise trifluoroacetic anhydride (0.46 g, 2.2 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 (0.383 g, 1.00 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.

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

Sources & evidence

ORD record
ord-b846a61b0bc843ab80d02d74411a01af
Source dataset
uspto-grants-2015_11
Patent number
US09174967B2

Linked notes

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