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Tin dichloride dihydrate → Tert-butyl 4-((5-amino-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylate

HRID 384630
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HRID 384630 반응식
O.[Sn](Cl)Cl.[C:5]([C:7]1[N:8]=[CH:9][C:10]([NH:13][C:14]2[CH:19]=[C:18]([NH:20][CH2:21][CH:22]3[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]3)[C:17]([N+:35]([O-])=O)=[CH:16][N:15]=2)=[N:11][CH:12]=1)#[N:6]>C(O)C>[NH2:35][C:17]1[C:18]([NH:20][CH2:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]2)=[CH:19][C:14]([NH:13][C:10]2[CH:9]=[N:8][C:7]([C:5]#[N:6])=[CH:12][N:11]=2)=[N:15][CH:16]=1
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참가 물질

4

반응물 2

HCID 43835034Tin dichloride dihydrateHCID 66746238Tert-butyl 4-((2-(5-cyanopyrazin-2-ylamino)-5-nitropyridin-4-ylamino)methyl)piperidine-1-carboxylate

생성물 1

HCID 59613544Tert-butyl 4-((5-amino-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylate수율 91.4%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
70 °C

실험 절차

Tin (II) chloride hydrate (678 mg, 5 eq) was added to a solution of tert-butyl 4-((2-(5-cyanopyrazin-2-ylamino)-5-nitropyridin-4-ylamino)methyl)piperidine-1-carboxylate (273 mg) in ethanol (20 mL). The mixture was heated at 70° C. for 30 minutes then cooled to room temperature and evaporated to dryness. The residue was diluted with ethyl acetate and saturated aqueous sodium hydrogen carbonate. The suspension was filtered and the aqueous phase was separated and extracted twice with ethyl acetate. The combined organic layers were dried (Na2SO4) and concentrated to give crude tert-butyl 4-((5-amino-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylate (233 mg) as a yellow solid.

후처리

  1. temperaturethen cooled to room temperature
  2. customevaporated to dryness
  3. additionThe residue was diluted with ethyl acetate and saturated aqueous sodium hydrogen carbonate
  4. filtrationThe suspension was filtered
  5. customthe aqueous phase was separated
  6. extractionextracted twice with ethyl acetate
  7. dry with materialThe combined organic layers were dried (Na2SO4)
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-186a22e5dca84f219013e78b48374251
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08367658B2

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