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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 1474382
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HRID 1474382 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 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

생성물 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

시약·촉매·용매

2
HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-839df658af714703839f29de0b856dad
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09018211B2

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