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Sodium hydride → (+/-)-1,1-dimethylethyl 4-[[1-[2-hydroxy-2-(6-methyl-2-pyridinyl)ethyl]-1H-benzimidazol-2-yl]amino]-1-piperidinecarboxylate

HRID 349208
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인쇄 미리보기

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HRID 349208 반응식
[H-].[Na+].[NH:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[NH:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.[O:26]1[CH:28]([C:29]2[N:34]=[C:33]([CH3:35])[CH:32]=[CH:31][CH:30]=2)[CH2:27]1>CN(C)C=O>[OH:26][CH:28]([C:29]1[CH:30]=[CH:31][CH:32]=[C:33]([CH3:35])[N:34]=1)[CH2:27][N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[NH:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1
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참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 219281642-Methyl-6-(oxiran-2-yl)pyridineHCID 22036999tert-Butyl 4-((1H-benzo[d]imidazol-2-yl)amino)piperidine-1-carboxylate

생성물 1

HCID 22711809(+/-)-1,1-dimethylethyl 4-[[1-[2-hydroxy-2-(6-methyl-2-pyridinyl)ethyl]-1H-benzimidazol-2-yl]amino]-1-piperidinecarboxylate수율 38.8%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매
2회

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온도
40 °C

실험 절차

Reaction under N2 flow. NaH 60% (0.02 mol) was added to a mixture of 1,1-dimethyl-ethyl 4-(1H-benzimidazol-2-ylamino)-1-piperidinecarboxylate (0.02 mol) in N,N-di-methylformamide (100 ml). The mixture was stirred at 40° C. for 1 hour. 6-(Epoxyethyl)-2-picoline (0.02 mol) in a small amount of N,N-dimethylformamide was added. The mixture was stirred at 100° C. overnight. The solvent was evaporated. The residue was taken up in H2O and CH2Cl2. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5 and 90/10). The pure fractions were collected and the solvent was evaporated, yielding 3.5 g of (±)-1,1-dimethylethyl 4-[[1-[2-hydroxy-2-(6-methyl-2-pyridinyl)ethyl]-1H-benzimidazol-2-yl]amino]-1-piperidinecarboxylate (interm. 16).

후처리

  1. customReaction under N2 flow
  2. stirringThe mixture was stirred at 100° C. overnight
  3. customThe solvent was evaporated
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5 and 90/10)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-b294c0be88ae4a01b6cfb1dc7aba0a17
출처 데이터셋
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07179811B2

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