m-Chloroperbenzoic acid → 2-(4-Fluorophenyl)-1-(2-(1-(s)-phenylethyl)amino-4-pyrimidinyl)-5-(4-tert.butoxycarbonyl-1-piperazinyl)imidazo[4,5-b]pyridine

HRID 396380

반응식

HRID 396380 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:30]3[CH:35]=[CH:34][N:33]=[C:32](SC)[N:31]=3)[C:10]3[C:11]([N:29]=2)=[N:12][C:13]([N:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)=[CH:14][CH:15]=3)=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=O)C=1.[C:49]1([C@@H:55]([NH2:57])[CH3:56])[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>C(Cl)Cl.CC(O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:30]3[CH:35]=[CH:34][N:33]=[C:32]([NH:57][C@H:55]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[CH3:56])[N:31]=3)[C:10]3[C:11]([N:29]=2)=[N:12][C:13]([N:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)=[CH:14][CH:15]=3)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 70297m-Chloroperbenzoic acidHCID 758181-Phenethylamine, (-)-HCID 224861592-(4-Fluorophenyl)-1-(2-methylthio-4-pyrimidinyl)-5-(4-tert.butoxycarbonyl-1-piperazinyl)imidazo[4,5-b]pyridine

생성물 1

HCID 213545192-(4-Fluorophenyl)-1-(2-(1-(s)-phenylethyl)amino-4-pyrimidinyl)-5-(4-tert.butoxycarbonyl-1-piperazinyl)imidazo[4,5-b]pyridine수율 35%

시약·촉매·용매 1

HCID 21922555Acetic acid methylene chloride용매

반응 조건

온도
120 °C

실험 절차

2-(4-Fluorophenyl)-1-(2-methylthio-4-pyrimidinyl)-5-(4-tert.butoxycarbonyl-1-piperazinyl)imidazo[4,5-b]pyridine (106 mg, 0.2 mmol) is dissolved in CH2Cl2/HOAc 1:1 (10 ml), combined with mCPBA (113 mg 70%, 0.24 mmol) and stirred for 15 min. The reaction mixture is poured on water and extracted with CH2Cl2 three times. The combined organic phases are dried over Na2SO4. filtered and evaporated to dryness to yield the crude sulfoxide (100 mg), which is dissolved in 1-(S)-phenylethylamine (0.2 ml) and heated to 120° C. for 1 h. Purification over SiO2 (acetone/hexanes 1:1) yielded the title compound as colorless foam (45 mg 35%)

후처리

  1. additionThe reaction mixture is poured on water
  2. extractionextracted with CH2Cl2 three times
  3. dry with materialThe combined organic phases are dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customto yield the crude sulfoxide (100 mg), which
  7. customPurification over SiO2 (acetone/hexanes 1:1)

출처 및 근거

ORD 기록
ord-01a57e2ac74e44b59c31bb25a522d7f1
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06608072B1

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