Triethylamine → HCID 22906481, compound

HRID 1488784Notes

Reaction equation

HRID 1488784 reaction equation
[CH2:1]([CH:3]([O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:25])[CH:12]=[C:13]([S:17][C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)[O:14]2)=[C:9]([OH:26])[C:8]=1[O:27][CH3:28])[CH2:4][CH3:5])[CH3:2].Cl.Cl.[CH3:31][N:32]1[CH2:37][CH2:36][N:35]([CH2:38][C:39]2[CH:47]=[CH:46][C:42]([CH2:43][O:44]Cl)=[CH:41][CH:40]=2)[CH2:34][CH2:33]1.C(N(CC)CC)C>ClCCl>[CH2:1]([CH:3]([O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:25])[CH:12]=[C:13]([S:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][C:43](=[O:44])[C:42]4[CH:41]=[CH:40][C:39]([CH2:38][N:35]5[CH2:34][CH2:33][N:32]([CH3:31])[CH2:37][CH2:36]5)=[CH:47][CH:46]=4)=[CH:20][CH:19]=3)[O:14]2)=[C:9]([OH:26])[C:8]=1[O:27][CH3:28])[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22906534HCID 22906534, compoundHCID 67705568HCID 67705568, compound

Product 1

HCID 22906481HCID 22906481, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

150 ml in dichloromethane of 4.46 g of 7-(1-ethylpropoxy)-5-hydroxy-2-(4-hydroxyphenylthio)-6-methoxychromone obtained in Example 33, 7.21 g of 4-(4-methylpiperazinomethyl)benzoxychloride dihydrochloride, 7.78 ml of triethylamine was stirred over 3 hours at room temperature. The solution thus reacted was concentrated, and an aqueous solution of sodium bicarbonate was added to the resulting residues, and the product was extracted with ethyl acetate. The organic layer was concentrated, and the residues thus obtained were purified by flash column chromatography (chloroform:methanol=30:1), whereby 2.31 g of 7-(1-ethylpropoxy)-5-hydroxy-2-{4-[4-(4-methylpiperazinomethyl)benzoyloxy]phenylthio}-6-methoxychromone was obtained.

Workup

  1. customThe solution thus reacted
  2. concentrationwas concentrated
  3. additionan aqueous solution of sodium bicarbonate was added to the resulting residues
  4. extractionthe product was extracted with ethyl acetate
  5. concentrationThe organic layer was concentrated
  6. customthe residues thus obtained
  7. customwere purified by flash column chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-6f044b2ac8ad4ab095d375d3cfc2e3b3
Source dataset
uspto-grants-1997_10
Patent number
US05675023

Reaction notes

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