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Acetic Acid → 4-(2-{4-[2-(Ethyloxy)-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)-2-(methyloxy)benzonitrile

HRID 1187125
ノート
印刷プレビュー

反応式

HRID 1187125 の反応式
Cl.[CH2:2]([O:4][CH:5]([C:13]1[CH:22]=[CH:21][C:16]2[C:17](=[O:20])[O:18][CH2:19][C:15]=2[C:14]=1[CH3:23])[CH2:6][N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)[CH3:3].[CH3:24][O:25][C:26]1[CH:33]=[C:32]([CH2:34][CH:35]=O)[CH:31]=[CH:30][C:27]=1[C:28]#[N:29].C([BH3-])#N.[Na+].CC(O)=O>CO.CCOC(C)=O>[CH2:2]([O:4][CH:5]([C:13]1[CH:22]=[CH:21][C:16]2[C:17](=[O:20])[O:18][CH2:19][C:15]=2[C:14]=1[CH3:23])[CH2:6][N:7]1[CH2:12][CH2:11][N:10]([CH2:35][CH2:34][C:32]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[C:26]([O:25][CH3:24])[CH:33]=2)[CH2:9][CH2:8]1)[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 675175415-[1-(ethyloxy)-2-piperazin-1-ylethyl]-4-methyl-2-benzofuran-1(3H)-one hydrochlorideHCID 772312592-(Methyloxy)-4-(2-oxoethyl)benzonitrile

生成物 1

HCID 498010444-(2-{4-[2-(Ethyloxy)-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)-2-(methyloxy)benzonitrile

試薬・触媒・溶媒

2
HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

5-[1-(Ethyloxy)-2-piperazin-1-ylethyl]-4-methyl-2-benzofuran-1(3H)-one hydrochloride (50 mg, 0.16 mmol), 2-(methyloxy)-4-(2-oxoethyl)benzonitrile (40 mg, 0.23 mmol), sodium cyanoborohydride (14 mg, 1.7 mmol) and a stir bar were added to a 25 mL flask and few drops of AcOH. The resulting mixture was then dissolved in MeOH (3 mL) and stirred for 12 h; Analysis by LC indicated that reaction had gone to completion. The reaction mixture was treated with EtOAc (20 mL) and washed with aq. NaHCO3 and aq. NaCl. The organic phase was then dried over Na2SO4, filtered and concentrated to dryness; the resulting residue was then dissolved in MeOH (3.5 mL), filtered and shot into Mass-directed HPLC for separation to give the desired product. LC-MS (IE, m/z): 464 [M+1]+.

後処理

  1. customAnalysis by LC indicated that reaction
  2. washwashed with aq. NaHCO3 and aq. NaCl
  3. dry with materialThe organic phase was then dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. dissolutionthe resulting residue was then dissolved in MeOH (3.5 mL)
  7. filtrationfiltered
  8. customshot into Mass-directed HPLC for separation

出典と根拠

ORDレコード
ord-217a7a66d1d3401cb3c1c0f56c6dd879
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08673920B2

反応ノート

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