Stannous chloride dihydrate → tert-Butyl 4-((5-amino-2-(5-cyanopyrazin-2-ylamino)pyridin-4-yloxy)methyl)piperidine-1-carboxylate

HRID 556811ノート

反応式

HRID 556811 の反応式
O.O.[Sn](Cl)Cl.[C:6]([C:8]1[N:9]=[CH:10][C:11]([NH:14][C:15]2[CH:20]=[C:19]([O:21][CH2:22][CH:23]3[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]3)[C:18]([N+:36]([O-])=O)=[CH:17][N:16]=2)=[N:12][CH:13]=1)#[N:7]>C(O)C>[NH2:36][C:18]1[C:19]([O:21][CH2:22][CH:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]2)=[CH:20][C:15]([NH:14][C:11]2[CH:10]=[N:9][C:8]([C:6]#[N:7])=[CH:13][N:12]=2)=[N:16][CH:17]=1

参加物

4

反応物 2

HCID 61436Stannous chloride dihydrateHCID 59613322Tert-butyl 4-((2-(5-cyanopyrazin-2-ylamino)-5-nitropyridin-4-yloxy)methyl)piperidine-1-carboxylate

生成物 1

HCID 59613369tert-Butyl 4-((5-amino-2-(5-cyanopyrazin-2-ylamino)pyridin-4-yloxy)methyl)piperidine-1-carboxylate収率 89%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
78 °C

実験手順

Tin (II) chloride dihydrate (745 mg, 3.3 mmol) was added to a solution of crude tert-butyl 4-((2-(5-cyanopyrazin-2-ylamino)-5-nitropyridin-4-yloxy)methyl)piperidine-1-carboxylate (301 mg, 0.66 mmol) in ethanol. After heating at 78° C. for 2 hours the mixture was cooled to room temperature and concentrated. The residue was diluted with ethyl acetate and water and the resulting precipitate was removed by filtration. The biphasic filtrate was separated and the aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated to give a brown solid (250 mg). A portion of the crude material was purified by preparative HPLC to give tert-butyl 4-((2-(5-cyanopyrazin-2-ylamino)-5-nitropyridin-4-yloxy)methyl) piperidine-1-carboxylate (16 mg) as a yellow powder.

後処理

  1. temperaturewas cooled to room temperature
  2. concentrationconcentrated
  3. additionThe residue was diluted with ethyl acetate and water
  4. customthe resulting precipitate was removed by filtration
  5. customThe biphasic filtrate was separated
  6. extractionthe aqueous phase was extracted with ethyl acetate
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-230d0b0c168f4f82aa96fe1e3ab89b74
出典データセット
uspto-grants-2011_11
特許番号
US08058045B2

反応ノート

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