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

HRID 1474380
Notes
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Reaction equation

HRID 1474380 reaction equation
Cl.[F:2][CH:3]([C:11]1[CH:20]=[CH:19][C:14]2[C:15](=[O:18])[O:16][CH2:17][C:13]=2[C:12]=1[CH3:21])[CH2:4][N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.[CH3:22][O:23][C:24]1[CH:31]=[C:30]([CH2:32][CH:33]=O)[CH:29]=[CH:28][C:25]=1[C:26]#[N:27].C([BH3-])#N.[Na+].CO>CC(O)=O>[F:2][CH:3]([C:11]1[CH:20]=[CH:19][C:14]2[C:15](=[O:18])[O:16][CH2:17][C:13]=2[C:12]=1[CH3:21])[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH2:33][CH2:32][C:30]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24]([O:23][CH3:22])[CH:31]=2)[CH2:7][CH2:6]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 666467295-(1-fluoro-2-piperazin-1-ylethyl)-4-methyl-2-benzofuran-1(3H)-one hydrochlorideHCID 772312592-(Methyloxy)-4-(2-oxoethyl)benzonitrile

Product 1

HCID 498010424-(2-{4-[2-Fluoro-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)-2-(methyloxy)benzonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-(1-Fluoro-2-piperazin-1-ylethyl)-4-methyl-2-benzofuran-1(3H)-one hydrochloride (30 mg, 0.11 mmol), 2-(methyloxy)-4-(2-oxoethyl)benzonitrile (37 mg, 0.22 mmol), sodium cyanoborohydride (67 mg, 1.078 mmol) were added to a 25 mL flask containing a stir bar; to the flask was added MeOH (3 mL) and few drops of AcOH. The reaction mixture was subsequently stirred for 12 hr; LC indicated that reaction had gone to completion. The solution was concentrated to dryness, redissolved in EtOAc (15 mL) and washed with aq. NaHCO3 and aq. NaCl. The organic phase was dried over Na2SO4, filtered and concentrated to dryness. It was then re-dissolved in MeOH (3.5 mL) again, filtered and shot into mass-directed HPLC for separation to give the desired product. LC-MS (IE, m/z): 450 [M+1]+.

Workup

  1. additioncontaining a stir bar
  2. customLC indicated that reaction
  3. concentrationThe solution was concentrated to dryness
  4. dissolutionredissolved in EtOAc (15 mL)
  5. washwashed with aq. NaHCO3 and aq. NaCl
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. dissolutionIt was then re-dissolved in MeOH (3.5 mL) again
  10. filtrationfiltered
  11. customshot into mass-directed HPLC for separation

Sources & evidence

ORD record
ord-0a44c8d3f3be4717b49e108875c80d26
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09018211B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes