m-Chloroperbenzoic acid → HCID 10184433, compound

HRID 1796562Notes

Reaction equation

HRID 1796562 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:5]2[N:14]=[C:15]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([S:23][CH3:24])[N:18]=3)=[C:4]2[CH:3]=1.C(=O)(O)[O-:34].[Na+].ClC1C=C(C=CC=1)C(OO)=O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[N:5]2[N:14]=[C:15]([C:25]3[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([S:23]([CH3:24])=[O:34])[N:18]=3)=[C:4]2[CH:3]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 10276682HCID 10276682, compound

Product 1

HCID 10184433HCID 10184433, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-{5-chloro-2-(4-methoxyphenyl)-3-[2-(methylsulfanyl)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-7-yl}-N-cyclopentylamine (133 mg, 0.28 mmol) in chloroform (10 mL) was added sodium bicarbonate (24 mg, 0.28 mmol). The reaction mixture was cooled to 0° C. m-Chloroperoxybenzoic acid (57˜86%, 86 mg, 0.50 mmol) was added. After stirring at 0° C. for 1.5 hours, the reaction mixture was quenched by addition of aqueous sodium bicarbonate and the resulting mixture extracted with dichloromethane. The organics were combined and washed with water, then dried over magnesium sulfate. Filtration and concentration followed by chromatography (19:1 dichloromethane/methanol) gave N-{5-chloro-2-(4-methoxyphenyl)-3-[2-(methylsulfinyl)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-7-yl}-N-cyclopentylamine (121 mg, 88%) as a yellow solid. 1H NMR (CDCl3) δ 8.43 (d, 1H), 7.93 (d, 1H), 7.51 (d, 2H), 7.00 (d, 2H), 6.98 (d, 1H), 6.11 (d, 1H), 6.08 (d, 1H), 3.96 (m, 1H), 3.88 (s, 3H), 2.99 (s, 3H), 2.13 (m, 2H), 1.82–1.66 (m, 6H). MS m/z 482 (M+1).

Workup

  1. additionwas added
  2. customthe reaction mixture was quenched by addition of aqueous sodium bicarbonate
  3. extractionthe resulting mixture extracted with dichloromethane
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-21ee0b9dba064b3eae45337415bcf134
Source dataset
uspto-grants-2006_04
Patent number
US07030134B2

Reaction notes

Loading…