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Triethylamine → HCID 57591440, compound

HRID 1784144
Notes
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Reaction equation

HRID 1784144 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH2:24]([O:31][C:32](=[O:43])[CH:33]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:34](O)=[O:35])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(CC)CC>CN(C=O)C>[CH2:24]([O:31][C:32](=[O:43])[CH:33]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:34]([N:11]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:22])([F:21])[F:23])=[CH:16][CH:15]=1)=[O:35])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 117278Propanedioic acid, 2-phenyl-, 1-(phenylmethyl) esterHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 57591499HCID 57591499, compound

Product 1

HCID 57591440HCID 57591440, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.7 g (2.1 mmol) (3,4-Dimethoxy-phenyl)-[2-(4-trifluoromethyl-phenyl)-ethyl]-amine, 0.58 g (2.1 mmol) 2-phenyl-malonic acid monobenzylester (commercially available), 0.83 g (2.5 mmol) TBTU and 0.43 g (4.3 mmol) NEt3 in 15 mL DMF was stirred at room temperature for 16 h. After evaporation to dryness the residue was treated with HCl aq. and DCM. The combined organic phases were washed with HCl aq., dried with MgSO4 and evaporated to dryness. The residue was purified by flash column chromatography on silica eluting with a gradient formed from ethyl acetate and heptane. The product containing fractions were combined and evaporated to dryness to yield 0.35 g (29%) of the title compound. MS(m/e): 578.3 (MH+).

Workup

  1. customAfter evaporation to dryness the residue
  2. additionwas treated with HCl aq. and DCM
  3. washThe combined organic phases were washed with HCl aq.
  4. dry with materialdried with MgSO4
  5. customevaporated to dryness
  6. customThe residue was purified by flash column chromatography on silica eluting with a gradient
  7. customformed from ethyl acetate and heptane
  8. additionThe product containing fractions
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-b788071888c243319146f7e8d516f378
Source dataset
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07501541B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes