Diisopropylethylamine → HCID 57591454, compound

HRID 1784147Notes

Reaction equation

HRID 1784147 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:22][N:23]([CH3:36])[C:24](=[O:35])[CH:25]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:26](O)=[O:27].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[C:26](=[O:27])[CH:25]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:24]([N:23]([CH3:36])[CH3:22])=[O:35])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 57591490HCID 57591490, compound2×HCID 67084392HCID 67084392, compound

Product 1

HCID 57591454HCID 57591454, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 28.7 mg (0.1 mmol) [2-(3,4-Dimethoxy-phenyl)-ethyl]-(4-methoxy-phenyl)-amine (intermediate 2), 20.7 mg (0.1 mmol) N,N-Dimethyl-2-phenyl-malonamic acid (WO2000009481), 38.5 mg (0.12 mmol) TBTU and 38.7 mg (0.3 mmol) DIPEA in 3 mL DMF was stirred at room temperature for 16 h. The mixture was concentrated diluted with methanol and formic acid and purified by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid, the product containing fractions were evaporated to yield 23.2 mg (61%) of the title compound. MS(m/e): 477.2 (MH+).

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with methanol and formic acid
  3. custompurified by preparative HPLC on reversed phase
  4. washeluting with a gradient
  5. customformed from acetonitrile, water and formic acid
  6. additionthe product containing fractions
  7. customwere evaporated

Sources & evidence

ORD record
ord-34500abe57a04c3db6dfd547c5979406
Source dataset
uspto-grants-2009_03
Patent number
US07501541B2

Reaction notes

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