Hy-drazinium monoformate → (R)-N-(2-(1H-1,2,3-Triazol-1-yl)ethyl)-4-(7-(5-(1-aminoethyl)-2-fluoropyridin-4-yl)benzo[b]thiophen-2-yl)pyrimidin-2-amine

HRID 1640936노트

반응식

HRID 1640936 반응식
NN.C(O)=O.[N:6]1([CH2:11][CH2:12][NH:13][C:14]2[N:19]=[C:18]([C:20]3[S:24][C:23]4[C:25]([C:29]5[C:34]([C@H:35]([N:37]=[N+]=[N-])[CH3:36])=[CH:33][N:32]=[C:31]([F:40])[CH:30]=5)=[CH:26][CH:27]=[CH:28][C:22]=4[CH:21]=3)[CH:17]=[CH:16][N:15]=2)[CH:10]=[CH:9][N:8]=[N:7]1>C(O)C.[Ni]>[N:6]1([CH2:11][CH2:12][NH:13][C:14]2[N:19]=[C:18]([C:20]3[S:24][C:23]4[C:25]([C:29]5[C:34]([C@H:35]([NH2:37])[CH3:36])=[CH:33][N:32]=[C:31]([F:40])[CH:30]=5)=[CH:26][CH:27]=[CH:28][C:22]=4[CH:21]=3)[CH:17]=[CH:16][N:15]=2)[CH:10]=[CH:9][N:8]=[N:7]1

참가 물질

5

반응물 2

HCID 46899473Hy-drazinium monoformateHCID 86641882(R)-N-(2-(1H-1,2,3-triazol-1-yl)ethyl)-4-(7-(5-(1-azidoethyl)-2-fluoropyridin-4-yl)benzo[b]thiophen-2-yl)pyrimidin-2-amine

생성물 1

HCID 59332526(R)-N-(2-(1H-1,2,3-Triazol-1-yl)ethyl)-4-(7-(5-(1-aminoethyl)-2-fluoropyridin-4-yl)benzo[b]thiophen-2-yl)pyrimidin-2-amine수율 85%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 702Ethanol용매

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온도
0 °C

실험 절차

Add NH2NH2—HCOOH (Pre-prepared, 1 mL) to a solution of (R)—N-(2-(1H-1,2,3-triazol-1-yl)ethyl)-4-(7-(5-(1-azidoethyl)-2-fluoropyridin-4-yl)benzo[b]thiophen-2-yl)pyrimidin-2-amine (250 mg, 513.84 μmol) in ethanol (10 mL). Cool the mixture to 0° C. and add Raney Nickel (0.5 g, 8.52 mmol, wet with water as it packed). Stir the solution at RT for another 1.5 h, filter Raney Nickel out, and wash with methanol. Dilute filtrate with chloroform/IPA (3/1) and wash with saturated sodium carbonate. Dry the organic phase over sodium sulfate and concentrate in vacuo to give a brown tar. Purify the solid by passing through a FCC (10% methanol in DCM) to give the title compound as a pale brown solid (200 mg, 85%). MS (ES) m/z 461 [M+1]+.

후처리

  1. filtrationfilter Raney Nickel out
  2. washwash with methanol
  3. washDilute filtrate with chloroform/IPA (3/1) and wash with saturated sodium carbonate
  4. dry with materialDry the organic phase over sodium sulfate
  5. concentrationconcentrate in vacuo
  6. customto give a brown tar
  7. customPurify the solid

출처 및 근거

ORD 기록
ord-ad8a51b426324816b9005d1675942a88
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08114872B2

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