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Acetic Acid → 7-(3-Benzylaminomethyl-1-pyrrolyl)-1-(ethoxycarbonylmethyl)-6-trifluoromethyl-2,3(1H,4H)-quinoxalinedione

HRID 861539
Notes
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Reaction equation

HRID 861539 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:16]2[C:11](=[CH:12][C:13]([C:24]([F:27])([F:26])[F:25])=[C:14]([N:17]3[CH:21]=[CH:20][C:19]([CH:22]=O)=[CH:18]3)[CH:15]=2)[NH:10][C:9](=[O:28])[C:8]1=[O:29])=[O:5])[CH3:2].[CH2:30]([NH2:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C>[CH2:30]([NH:37][CH2:22][C:19]1[CH:20]=[CH:21][N:17]([C:14]2[CH:15]=[C:16]3[C:11]([NH:10][C:9](=[O:28])[C:8](=[O:29])[N:7]3[CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:12][C:13]=2[C:24]([F:25])([F:27])[F:26])[CH:18]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5003444Sodium cyanoborohydrideHCID 153379971-(Ethoxycarbonylmethyl)-7-(3-formyl-1-pyrrolyl)-6-trifluoromethyl-2,3(1H,4H)-quinoxalinedione

Product 1

HCID 220972147-(3-Benzylaminomethyl-1-pyrrolyl)-1-(ethoxycarbonylmethyl)-6-trifluoromethyl-2,3(1H,4H)-quinoxalinedioneYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.2 g (2.9 mmol) of the compound of Example 70, 0.31 g (2.9 mmol) of benzylamine and 0.2 ml (2.9 mmol) of acetic acid were dissolved in 50 ml of ethanol and, at room temperature, 0.18 g (2.9 mmol) of sodium cyanoborohydride was added a little at a time. The mixture was stirred for 16 h and then concentrated under reduced pressure, and the organic phase was dried and finally concentrated again under reduced pressure. The residue was purified by chromatography on silica gel (mobile phase: methylene chloride/methanol=5:1) to yield 0.87 g (60%) of the product.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe organic phase was dried
  3. concentrationfinally concentrated again under reduced pressure
  4. customThe residue was purified by chromatography on silica gel (mobile phase: methylene chloride/methanol=5:1)

Sources & evidence

ORD record
ord-1c9b85427c344a31ad7d606e15a71f8b
Source dataset
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05714489

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes