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Diisopropylethylamine → N-(5-(3,3-difluoropiperidin-1-yl)-1-(2-((trimethylsilyl)methoxy)ethyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 1466654
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HRID 1466654 반응식
[F:1][C:2]1([F:22])[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[N:12]([CH2:13][CH2:14][O:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:11]=[CH:10][C:9]=2[NH2:21])[CH2:3]1.CCN(C(C)C)C(C)C.[N:32]1[N:36]2[CH:37]=[CH:38][CH:39]=[N:40][C:35]2=[C:34]([C:41](Cl)=[O:42])[CH:33]=1>C1COCC1>[F:22][C:2]1([F:1])[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[N:12]([CH2:13][CH2:14][O:15][CH2:16][Si:17]([CH3:19])([CH3:18])[CH3:20])[N:11]=[CH:10][C:9]=2[NH:21][C:41]([C:34]2[CH:33]=[N:32][N:36]3[CH:37]=[CH:38][CH:39]=[N:40][C:35]=23)=[O:42])[CH2:3]1
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참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 19623233Pyrazolo[1,5-a]pyrimidine-3-carbonyl chlorideHCID 668507645-(3,3-difluoropiperidin-1-yl)-1-(2-((trimethylsilyl)methoxy)ethyl)-1H-pyrazol-4-amine

생성물 1

HCID 66850749N-(5-(3,3-difluoropiperidin-1-yl)-1-(2-((trimethylsilyl)methoxy)ethyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide수율 60%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

To a solution of 5-(3,3-difluoropiperidin-1-yl)-1-(2-((trimethylsilyl)methoxy)ethyl)-1H-pyrazol-4-amine (1.2 g, 3.61 mmol) in 30 mL THF was added DIPEA (1.3 mL, 7.22 mmol) and pyrazolo[1,5-a]pyrimidine-3-carbonyl chloride (720 mg, 3.97 mmol) in THF (50 mL) at 0° C. After addition was complete, the mixture was warmed to room temperature, then stirred overnight. The mixture was concentrated in vacuo and the residue was purified by silica gel column chromatogaphy (hexanes:EtOAc=3:1 to 1:1) to afford 1.0 g (60%) of N-(5-(3,3-difluoropiperidin-1-yl)-1-(2-((trimethylsilyl)methoxy)ethyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide. LCMS (ESI) m+H=478.2; 1H NMR (400 MHz, CDCl3) δ: 9.49 (s, 1H), 8.87 (dd, 1H), 8.75 (s, 1H), 8.71 (dd, 1H), 7.94 (s, 1H), 7.10 (dd, 1H), 5.40 (s, 2H), 3.67 (m, 6H), 2.06 (s, 2H), 1.93 (m, 2H), 0.95 (m, 2H), 0 (s, 9H).

후처리

  1. additionAfter addition
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was purified by silica gel column chromatogaphy (hexanes:EtOAc=3:1 to 1:1)

출처 및 근거

ORD 기록
ord-8a5dbd67044b4f0c8a6f14ec1f9f61e8
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08999998B2

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