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Tetrahydro-4H-pyran-4-one → HCID 69122283, 화합물

HRID 2064094
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인쇄 미리보기

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HRID 2064094 반응식
[ClH:1].[F:2][CH:3]([F:21])[O:4][C:5]1[CH:6]=[CH:7][C:8]2[NH:12][C:11](=[O:13])[N:10]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[C:9]=2[CH:20]=1.[O:22]1[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(N(CC)CC)C.ClCCCl>[ClH:1].[F:21][CH:3]([F:2])[O:4][C:5]1[CH:6]=[CH:7][C:8]2[NH:12][C:11](=[O:13])[N:10]([CH:14]3[CH2:15][CH2:16][N:17]([CH:25]4[CH2:26][CH2:27][O:22][CH2:23][CH2:24]4)[CH2:18][CH2:19]3)[C:9]=2[CH:20]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 57423922HCID 57423922, 화합물

생성물 1

HCID 69122283HCID 69122283, 화합물수율 68.6%

시약·촉매·용매 2

HCID 111,2-Dichloroethane
용매
HCID 8471Triethylamine용매

실험 절차

6-[(Difluoromethyl)oxy]-1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one hydrochloride (D54, 0.3 g) 1,2-dichloroethane (10 ml) and triethylamine (0.5 ml), tetrahydro-4H-pyran-4-one (0.6 g), sodium triacetoxyborohydride (0.6 g) was stirred at room temperature over 3 days. The mixture was poured into sodium bicarbonate solution and extracted with dichloromethane. The organic phase was separated, washed with brine and the solvent was removed and the residue was chromatographed on silica gel eluted with dichloromethane/2M ammonia in methanol 0-10%. The resulting product was dissolved in a mixture of methanol and dichloromethane, treated with 1M hydrogen chloride in ether and the solvent was removed. Recrystallisation from methanol gave the title compound as a white solid (0.26 g). Mass Spectrum 368 M+H+

후처리

  1. extractionextracted with dichloromethane
  2. customThe organic phase was separated
  3. washwashed with brine
  4. customthe solvent was removed
  5. customthe residue was chromatographed on silica gel
  6. washeluted with dichloromethane/2M ammonia in methanol 0-10%
  7. dissolutionThe resulting product was dissolved in a mixture of methanol and dichloromethane
  8. additiontreated with 1M hydrogen chloride in ether
  9. customthe solvent was removed
  10. customRecrystallisation from methanol

출처 및 근거

ORD 기록
ord-5b0e0ffdbf4e4ba996af0acf0883fa53
출처 데이터셋
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08288413B2

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