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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Hydrochloric Acid → 4-(2-{4-[2-Hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}-1-methylethyl)-2-(methyloxy)benzonitrile

HRID 1474383
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HRID 1474383 반응식
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([CH:11]([CH3:14])[CH:12]=O)[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].Cl.[OH:16][CH:17]([C:25]1[CH:34]=[CH:33][C:28]2[C:29](=[O:32])[O:30][CH2:31][C:27]=2[C:26]=1[CH3:35])[CH2:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>ClCCl>[OH:16][CH:17]([C:25]1[CH:34]=[CH:33][C:28]2[C:29](=[O:32])[O:30][CH2:31][C:27]=2[C:26]=1[CH3:35])[CH2:18][N:19]1[CH2:24][CH2:23][N:22]([CH2:12][CH:11]([C:9]2[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[C:3]([O:2][CH3:1])[CH:10]=2)[CH3:14])[CH2:21][CH2:20]1
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참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 5049666Sodium triacetoxyborohydrideHCID 666465015-(1-hydroxy-2-piperazin-1-ylethyl)-4-methyl-3H-2-benzofuran-1-one;hydrochlorideHCID 772312582-Methoxy-4-(1-oxopropan-2-yl)benzonitrile

생성물 1

HCID 498010454-(2-{4-[2-Hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}-1-methylethyl)-2-(methyloxy)benzonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To 2-methoxy-4-(1-oxopropan-2-yl)benzonitrile (0.020 g, 0.106 mmol) were added dichloromethane (15 mL) and 5-[1-hydroxy-2-(piperazin-1-yl)ethyl]-4-methyl-2-benzofuran-1(3H)-one hydrochloride [(0.037 g, 0.116 mmol), in dichloromethane (2 mL), and triethylamine (0.029 mL, 0.211 mmol)], and the mixture was stirred at room temperature for 0.5 h. Sodium triacetoxyborohydride (0.112 g, 0.529 mmol) was added, and the reaction mixture was stirred at room temperature for 24 h. The reaction was quenched with water (5 mL), and the organics were extracted with EtOAc (2×40 mL). The combined organic layers were washed with water (20 mL) and brine (20 mL) and dried (MgSO4). Filtration followed by concentration afforded an oily residue, which was purified via mass-directed reverse-phase HPLC followed by evaporation and drying of the pure fraction obtained which then converted to HCl salt by triturating in 1M HCl in diethyl ether (0.50 mL, 2 h). Evaporation and dried under vacuum provided 4-(2-{4-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}-1-methylethyl)-2-(methyloxy)benzonitrile.

후처리

  1. stirringthe reaction mixture was stirred at room temperature for 24 h
  2. customThe reaction was quenched with water (5 mL)
  3. extractionthe organics were extracted with EtOAc (2×40 mL)
  4. washThe combined organic layers were washed with water (20 mL) and brine (20 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration
  7. concentrationfollowed by concentration
  8. customafforded an oily residue, which
  9. customwas purified via mass-directed reverse-phase HPLC
  10. customfollowed by evaporation
  11. customdrying of the pure fraction
  12. customobtained which
  13. customby triturating in 1M HCl in diethyl ether (0.50 mL, 2 h)
  14. customEvaporation
  15. customdried under vacuum

출처 및 근거

ORD 기록
ord-66c4d3bc7a2849459b99bfc87fce10cc
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09018211B2

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