Sodium Carbonate → 2-(4-Fluorophenyl)-1-(2-(1-(S)-phenylethyl)amino-4-primidinyl)-5-aminoimidazo[4,5-b]pyridine

HRID 396376

반응식

HRID 396376 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:18]3[CH:23]=[CH:22][N:21]=[C:20](SC)[N:19]=3)[C:10]3[C:11]([N:17]=2)=[N:12][C:13]([NH2:16])=[CH:14][CH:15]=3)=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=O)C=1.C([O-])([O-])=O.[Na+].[Na+].[C:43]1([C@@H:49]([NH2:51])[CH3:50])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C(Cl)Cl.CC(O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:51][C@H:49]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[CH3:50])[N:19]=3)[C:10]3[C:11]([N:17]=2)=[N:12][C:13]([NH2:16])=[CH:14][CH:15]=3)=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 758181-Phenethylamine, (-)-HCID 224861302-(4-Fluorophenyl)-1-(2-methylthio-4-pyrimidinyl)-5-aminoimidazo[4,5-b]pyridine

생성물 1

HCID 98453052-(4-Fluorophenyl)-1-(2-(1-(S)-phenylethyl)amino-4-primidinyl)-5-aminoimidazo[4,5-b]pyridine수율 52%

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-aminoimidazo[4,5-b]pyridine (110 mg, 0.31 mmol) is dissolved in CH2Cl2/HOAc 1:1 (6.2 ml), combined at 0° C. with mCPBA (84 mg 70% 0.34 mmol) and stirred for 30 min. The reaction mixture is poured on 2N Na2CO3 and extracted with ethyl acetate three times. The combined organic phases are dried over Na2SO4, filtered and evaporated to dryness to yield the crude sulfoxide (110 mg). 50 mg are dissolved in 1-(S)-phenylethylamine (0.5 ml) and heated to 120° C. for 1 h. Purification over RP18 (CH3CN/Water 70/30 to 10/90) yielded the title compound as light brown foam (30 mg 52%)

후처리

  1. extractionextracted with ethyl acetate three times
  2. dry with materialThe combined organic phases are dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customto yield the crude sulfoxide (110 mg)
  6. customPurification over RP18 (CH3CN/Water 70/30 to 10/90)

출처 및 근거

ORD 기록
ord-e0517b94d44b489cb932683350041fdf
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06608072B1

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