m-Chloroperbenzoic acid → HCID 10295871, compound

HRID 1373814Notes

Reaction equation

HRID 1373814 reaction equation
[CH2:1]([NH:5][C:6]1[N:11]2[N:12]=[C:13]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([S:21][CH3:22])[N:16]=3)=[C:10]2[CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].ClC1C=CC=C(C(OO)=[O:38])C=1>C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH2:1]([NH:5][C:6]1[N:11]2[N:12]=[C:13]([C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=3)[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([S:21]([CH3:22])=[O:38])[N:16]=3)=[C:10]2[CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 69450353N-butyl-2-(4-fluorophenyl)-3-[2-(methylsulfanyl)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-7-amine

Product 1

HCID 10295871HCID 10295871, compoundYield 60.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a cold (0° C.) solution of N-butyl-2-(4-fluorophenyl)-3-[2-(methylsulfanyl)-4-pyrimidinyl]pyrazolo[1,5-α]pyridin-7-amine (1.51 g, 3.7 mmol) in 50 mL chloroform was added m-chloroperbenzoic acid (0.87 g, 70–75%, 3.7 mmol). The reaction was allowed to warm to rt. After stirring for 5 h, another 0.2 g m-chloroperbenzoic acid was added and the reaction was stirred for 15 min. The reaction was diluted with aqueous sodium bicarbonate and extracted with dichloromethane. The organic extracts were washed with brine, dried over magnesium sulfate and concentrated. The crude product was recrystallized from ethyl acetate-hexanes to afford N-butyl-2-(4-fluorophenyl)-3-[2-(methylsulfinyl)-4-pyrimidinyl]pyrazolo[1,5-α]pyridin-7-amine (0.95 g, 60%) as an orange solid. 1H NMR (CDCl3): δ 8.40 (broad, 1H), 7.99 (d, 1H), 7.58 (m, 2H), 7.45 (t, 1H), 7.20 (t, 2H), 6.94 (d, 1H), 6.13 (d, 1H), 6.10 (broad, 1H), 3.38 (m, 2H), 2.98 (s, 3H), 1.79–1.42 (m, 4H), 0.97 (t, 3H); MS m/z 422 (M−1).

Workup

  1. stirringthe reaction was stirred for 15 min
  2. extractionextracted with dichloromethane
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product was recrystallized from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-d972d2e3392c4dd092a9edf420c2d185
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

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