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Trimethylsilyl isocyanate → (S)-1-((1-(7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-yl)pyrrolidin-3-yl)methyl)urea

HRID 57611
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HRID 57611 반응식
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:22]=[C:21]([N:23]4[CH2:27][CH2:26][C@@H:25]([CH2:28][NH2:29])[CH2:24]4)[C:20]4[C:15](=[N:16][CH:17]=[CH:18][N:19]=4)[CH:14]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[Si]([N:43]=[C:44]=[O:45])(C)(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:22]=[C:21]([N:23]4[CH2:27][CH2:26][C@@H:25]([CH2:28][NH:29][C:44]([NH2:43])=[O:45])[CH2:24]4)[C:20]4[C:15](=[N:16][CH:17]=[CH:18][N:19]=4)[CH:14]=3)=[CH:9][CH:8]=2)[CH2:5][CH2:6]1
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반응물 4

HCID 70696Trimethylsilyl isocyanateHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 71113335(S)-(1-(7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-yl)pyrrolidin-3-yl)methanamine2회

생성물 1

HCID 71113801(S)-1-((1-(7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-yl)pyrrolidin-3-yl)methyl)urea

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of (S)-(1-(7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-yl)pyrrolidin-3-yl)methanamine (Compound 77, 0.16 mmol), DIPEA (207 mg, 1.6 mmol) and TMSNCO (184 mg, 1.6 mmol) in anhydrous CH2Cl2 (5 mL) was stirred at room temperature for 70 hours. The reaction mixture was poured into saturated NaHCO3 aqueous and extracted with CH2Cl2. The combined extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography to afford the title compound. MS (m/z): 434 (M+H)+.

후처리

  1. extractionextracted with CH2Cl2
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography

출처 및 근거

ORD 기록
ord-5c3a665de47048dc9e1878fa236fdf21
출처 데이터셋
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09434726B2

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