Triethylamine → HCID 178467689, compound

HRID 2290003Notes

Reaction equation

HRID 2290003 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16](I)=[CH:15][CH:14]=3)=[O:9])=[CH:4][CH:3]=1.[CH3:24][CH:25]([OH:28])[C:26]#[CH:27].CCN(CC)CC>CN(C=O)C>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([C:27]#[C:26][CH:25]([OH:28])[CH3:24])=[CH:15][CH:14]=3)=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 162393-Butyn-2-olHCID 178522879HCID 178522879, compound

Product 1

HCID 178467689HCID 178467689, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(4-chlorobenzyl)-4-hydroxy-6-iodo-3-quinolinecarboxamide from Example No. 40 (800 mg), 3-butyn-2-ol (0.20 mL), PdCl2 (PPh3)2 (32.3 mg), and 1.16 mL Et3N in 4.64 mL anhydrous DMF is heated at 90° C. for 1 hr. The reaction mixture is cooled to room temperature and partitioned between EtOAc and H2O. The aqueous layer is washed with EtOAc (3×). The combined organic layers are dried over Na2SO4 and condensed to obtain a red-brown residue. The residue is chromatographed eluting with 3% MeOH in CH2Cl2. Fractions homogenous by TLC are combined and condensed to afford 139.2 mg (20%) of the title compound as a brown solid.

Workup

  1. custompartitioned between EtOAc and H2O
  2. washThe aqueous layer is washed with EtOAc (3×)
  3. dry with materialThe combined organic layers are dried over Na2SO4 and condensed
  4. customto obtain a red-brown residue
  5. customThe residue is chromatographed
  6. washeluting with 3% MeOH in CH2Cl2
  7. customcondensed

Sources & evidence

ORD record
ord-cbc49b0260764d95b49e44f84f873b44
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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