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 1474382Notes

Reaction equation

HRID 1474382 reaction equation
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]

Participants

7

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-839df658af714703839f29de0b856dad
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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