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

HRID 396376

反応式

HRID 396376 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21922555Acetic acid methylene chloride溶媒

反応条件

温度
120 °C

実験手順

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%)

後処理

  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)

出典と根拠

ORDレコード
ord-e0517b94d44b489cb932683350041fdf
出典データセット
uspto-grants-2003_08
特許番号
US06608072B1

関連ノート

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