Di-tert-butyl peroxide → HCID 131735919, compound

HRID 2207428Notes

Reaction equation

HRID 2207428 reaction equation
[F:1][C:2]([F:38])([CH:8](OC(SC)=S)[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[C:19]([NH:21][C:22]3[N:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][N:23]=3)[CH:18]=[C:17]([CH3:32])[CH:16]=2)=[CH:11][N:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C1(P(=O)C2C=CC=CC=2)C=CC=CC=1.C(OOC(C)(C)C)(C)(C)C>O1CCOCC1>[F:38][C:2]([F:1])([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[C:19]([NH:21][C:22]3[N:27]=[C:26]([C:28]([F:29])([F:30])[F:31])[CH:25]=[CH:24][N:23]=3)[CH:18]=[C:17]([CH3:32])[CH:16]=2)=[CH:11][N:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 8033Di-tert-butyl peroxideHCID 254003Diphenylphosphine oxideHCID 131735918HCID 131735918, compound

Product 1

HCID 131735919HCID 131735919, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of ethyl 2,2-difluoro-3-{[(methylsulfanyl)carbonothioyl]oxy}-3-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]propanoate (68.5 mg, 0.120 mmol), anhydrous dioxane (5.00 mL), diphenylphosphine oxide (25.6 mg, 0.127 mmol) and di-tert-butyl peroxide (10.0 μL, 0.054 mmol) was heated to reflux for 6 hours under Ar(g). The reaction mixture was concentrate under reduced pressure and the residue was purified by reverse phase HPLC to afford ethyl 2,2-difluoro-3-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]propanoate. MS APCI C22H20F5N4O2 [M+H]+ 467. found 467.

Workup

  1. temperaturewas heated
  2. concentrationThe reaction mixture was concentrate under reduced pressure
  3. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-2cc43c8c2a784f41ad4bda49f1352b35
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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