Triethylamine → HCID 274126, compound

HRID 1296938Notes

Reaction equation

HRID 1296938 reaction equation
C(OC1C=C(OCC2C=CC=CC=2)C(Cl)=CC=1C1C(C2C=CC(CN)=CC=2)=CN(COCC[Si](C)(C)C)N=1)C1C=CC=CC=1.C(N(CC)CC)C.O=C1CCC(=O)N1[O:59][C:60](=[O:86])[C:61]1[CH:69]=[CH:68][C:67]([C:70]2[C:71]3[C:76]([O:77][C:78]4[C:83]=2[CH:82]=[CH:81][C:80](=[O:84])[CH:79]=4)=[CH:75][C:74]([OH:85])=[CH:73][CH:72]=3)=[C:63]([C:64]([OH:66])=[O:65])[CH:62]=1>C(Cl)Cl>[OH:85][C:74]1[CH:75]=[C:76]2[C:71](=[CH:72][CH:73]=1)[C:70]([C:67]1[C:63]([C:64]([OH:66])=[O:65])=[CH:62][C:61]([C:60]([OH:86])=[O:59])=[CH:69][CH:68]=1)=[C:83]1[C:78](=[CH:79][C:80](=[O:84])[CH:81]=[CH:82]1)[O:77]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4564399HCID 4564399, compoundHCID 58913532HCID 58913532, compound

Product 1

HCID 274126HCID 274126, compoundYield 111.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-[3-(2,4-bis-benzyloxy-5-chloro-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazol-4-yl]-benzylamine (0.02 g, 0.03 mmol) and triethylamine (0.02 ml, 0.15 mmol) in DCM (1 ml) was added 4-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-isophthalic acid 2,5-dioxo-pyrrolidin-1-yl ester (0.016 g, 0.03 mmol). The mixture was stirred at room temperature for 1 hour, then concentrated in vacuo. The mixture was purified by column chromatography using ethyl acetate and hexanes as eluent to give N-4-[3-(2,4-bis-benzyloxy-5-chloro-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazol-4-yl]-benzyl)-6-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-isophthalic acid as a yellow solid (0.0126 g, 40%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe mixture was purified by column chromatography

Sources & evidence

ORD record
ord-181b72dbeadf4ffa8b5cd1c49134aae0
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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