Triethylamine → (S)-3-methyl-2-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-ylamino)butanal

HRID 539015노트

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HRID 539015 반응식
[CH3:1][CH:2]([CH3:35])[C@H:3]([NH:6][C:7]1[CH:12]=[CH:11][N:10]2[N:13]=[CH:14][C:15]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4[N:23]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[CH:24]=[CH:25][N:26]=4)=[CH:18][CH:17]=3)=[C:9]2[N:8]=1)[CH2:4][OH:5].CCN(CC)CC>ClCCl.CS(C)=O.[Cl-].[Na+].O>[CH3:1][CH:2]([CH3:35])[C@H:3]([NH:6][C:7]1[CH:12]=[CH:11][N:10]2[N:13]=[CH:14][C:15]([C:16]3[CH:17]=[CH:18][C:19]([C:22]4[N:23]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:33])([CH3:32])[CH3:34])[CH:24]=[CH:25][N:26]=4)=[CH:20][CH:21]=3)=[C:9]2[N:8]=1)[CH:4]=[O:5]

참가 물질

6

반응물 2

HCID 8471TriethylamineHCID 67034614(S)-3-methyl-2-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-ylamino)butan-1-ol

생성물 1

HCID 86667823(S)-3-methyl-2-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-ylamino)butanal수율 88.4%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 6344Dichloromethane용매HCID 57417360Sodium chloride; water용매

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온도
-15 °C

실험 절차

To a stirred solution of (S)-3-methyl-2-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-ylamino)butan-1-ol (0.41 g, 0.83 mmol) in dichloromethane (6 mL) was added Et3N (0.58 mL, 4.2 mmol) at −15° C. A solution of pyridine-sulfur trioxide complex (0.66 g, 4.2 mmol) in DMSO (6 mL) was added in one portion. After stirring at −15° C. for 30 minutes, the mixture was poured into cold brine solution and extracted with ether. The combined organic extracts were washed with brine, dried and concentrated. The residue was purified by column chromatography (5% MeOH in dichloromethane) to give (S)-3-methyl-2-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-ylamino)butanal (0.36 g, 88%). LCMS (APCI+) m/z 491 [M+H]+.

후처리

  1. extractionextracted with ether
  2. washThe combined organic extracts were washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (5% MeOH in dichloromethane)

출처 및 근거

ORD 기록
ord-9f7419e12eb744baac93380f4a531a9b
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865726B2

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