m-Chloroperbenzoic acid → HCID 10295871, 화합물

HRID 1373814노트

반응식

HRID 1373814 반응식
[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]

참가 물질

5

반응물 2

HCID 70297m-Chloroperbenzoic acid2회HCID 69450353N-butyl-2-(4-fluorophenyl)-3-[2-(methylsulfanyl)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-7-amine

생성물 1

HCID 10295871HCID 10295871, 화합물수율 60.6%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 516892Sodium Bicarbonate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d972d2e3392c4dd092a9edf420c2d185
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07163940B2

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