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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
ノート
印刷プレビュー

反応式

HRID 1474383 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-66c4d3bc7a2849459b99bfc87fce10cc
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09018211B2

反応ノート

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