Monoperoxyphthalic Acid Magnesium Salt → HCID 59726837, compound

HRID 906865Notes

Reaction equation

HRID 906865 reaction equation
[F:1][C:2]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:3]=1[CH2:4][N:5]1[C:10]([C:11]2[S:12][C:13]([C:16]3[CH:21]=[C:20]([O:22][CH2:23][CH3:24])[N:19]=[C:18]([S:25][CH3:26])[N:17]=3)=[CH:14][CH:15]=2)=[CH:9][C:8]([C:27]([F:30])([F:29])[F:28])=[C:7]([C:31]#[N:32])[C:6]1=[O:33].[OH2:39].[OH2:40].O.O.O.O.C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=O.[Mg+2].C1C=C(C([O-])=O)C(C(O[O-])=O)=CC=1.[Mg+2]>ClCCl.CO>[F:1][C:2]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:3]=1[CH2:4][N:5]1[C:10]([C:11]2[S:12][C:13]([C:16]3[CH:21]=[C:20]([O:22][CH2:23][CH3:24])[N:19]=[C:18]([S:25]([CH3:26])(=[O:40])=[O:39])[N:17]=3)=[CH:14][CH:15]=2)=[CH:9][C:8]([C:27]([F:29])([F:30])[F:28])=[C:7]([C:31]#[N:32])[C:6]1=[O:33]

Participants

6

Reactant 3

HCID 10130449Monoperoxyphthalic Acid Magnesium SaltHCID 21894687Magnesium 2-(dioxidan-2-ide-1-carbonyl)benzoate--water (1/1/6)HCID 67389190HCID 67389190, compound

Product 1

HCID 59726837HCID 59726837, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

1-(2,4-Difluoro-benzyl)-6-[5-(6-ethoxy-2-methylsulfanyl-pyrimidin-4-yl)-thiophen-2-yl]-2-oxo-4-trifluoromethyl-1,2-dihydropyridine-3-carbonitrile (49 mg, 0.087 mmol) was dissolved in a mixture of dichloromethane (2 mL) and methanol (0.4 mL). To this solution was added magnesium monoperoxyphthalate hexahydrate, MMPP, (108 mg, 0.218 mmol, 80% tech.) and the mixture was stirred at ambient temperature for overnight. After this period the reaction mixture was combined with dichloromethene (20 mL) and was washed with 1M NaHCO3 (2×10 mL), and brine (10 mL). The resulting organic layer was separated and dried over anhydrous Na2SO4 and evaporated in vacuo to yield crude product. The crude product was purified using flash silica chromatography (25-50% EtOAc/Hexane) to yield 1-(2,4-difluorobenzyl)-6-[5-(6-ethoxy-2-methanesulfonyl-pyrimidin-4-yl)-thiophen-2-yl]-2-oxo-4-trifluoromethyl-1,2-dihydro-pyridine-3-carbonitrile (42 mg, 80%) as a yellow solid. 1H-NMR (CDCl3): δ 7.72 (m, 1H), 7.14 (m, 1H), 7.13 (m, 1H), 7.07 (s, 1H), 6.88 (m, 1H), 6.78 (m, 1H), 6.63 (s, 1H), 5.40 (s, 2H), 4.61 (q, J=7.1 Hz, 2H), 3.36 (s, 3H), 1.46 (t, J=7.1 Hz, 3H). MS (ES+): 597.2 (M+H).

Workup

  1. waitAfter this period the reaction mixture was combined with dichloromethene (20 mL)
  2. washwas washed with 1M NaHCO3 (2×10 mL), and brine (10 mL)
  3. customThe resulting organic layer was separated
  4. dry with materialdried over anhydrous Na2SO4
  5. customevaporated in vacuo
  6. customto yield crude product
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-096062d5f19348debbb25a431353cc5a
Source dataset
uspto-grants-2011_09
Patent number
US08013001B2

Reaction notes

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