2-(Benzenesulfonyl)-3-phenyloxaziridine → Methyl 2-(7-chloro-2-(3-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetate

HRID 472832Notes

Reaction equation

HRID 472832 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=3)[CH:10]=[C:6]2[N:5]=[C:4]([CH3:18])[C:3]=1[CH2:19][C:20]([O:22][CH3:23])=[O:21].C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1(C2[O:42]N2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1>C1COCC1>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=3)[CH:10]=[C:6]2[N:5]=[C:4]([CH3:18])[C:3]=1[CH:19]([OH:42])[C:20]([O:22][CH3:23])=[O:21]

Participants

5

Reactant 3

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 3251421Potassium bis(trimethylsilyl)amideHCID 86670274Methyl 2-(7-chloro-2-(3-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate

Product 1

HCID 86670273Methyl 2-(7-chloro-2-(3-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetateYield 51.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of methyl 2-(7-chloro-2-(3-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (7.8 g, 22.27 mmol) in THF (40 mL) at −78° C. was added KHMDS (44.5 mL, 22.27 mmol) dropwise over 30 min. The mixture was stirred at −78° C. for 30 min. A solution of 3-phenyl-2-(phenylsulfonyl)-1,2-oxaziridine (8.73 g, 33.4 mmol) in THF (50 mL) was added over 30 min and the reaction mixture was stirred for additional 2 h at −78° C. The reaction mixture was quenched with saturated NH4Cl aqueous solution (40 mL). The reaction mixture was allowed to warm to room temperature and then diluted with ethyl acetate (200 mL). The organic phase was washed with water and brine and dried with sodium sulfate. The solvent was evaporated. Purification by silica gel chromatography provided the title compound (4.2 g, 51.5%). 1H NMR (500 MHz, CHLOROFORM-d) δ 8.05-7.97 (m, 1H), 7.88 (dt, J=6.7, 1.8 Hz, 1H), 7.44-7.38 (m, 2H), 6.93 (s, 1H), 5.76 (s, 1H), 3.84 (s, 3H), 2.62 (s, 3H).

Workup

  1. stirringthe reaction mixture was stirred for additional 2 h at −78° C
  2. customThe reaction mixture was quenched with saturated NH4Cl aqueous solution (40 mL)
  3. temperatureto warm to room temperature
  4. additiondiluted with ethyl acetate (200 mL)
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried with sodium sulfate
  7. customThe solvent was evaporated
  8. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-ca834c3a519346b095fe9bb2beaaa7dd
Source dataset
uspto-grants-2014_01
Patent number
US08633200B2

Reaction notes

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