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 1640936ノート

反応式

HRID 1640936 の反応式
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

参加物

5

反応物 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

生成物 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-amine収率 85%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-ad8a51b426324816b9005d1675942a88
出典データセット
uspto-grants-2012_02
特許番号
US08114872B2

反応ノート

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