1-Hydroxybenzotriazole → HCID 20072843, compound

HRID 704632Notes

Reaction equation

HRID 704632 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([OH:10])=O)[N:6]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[N:33]1([C:39]2[CH:40]=[C:41]3[C:46](=[CH:47][CH:48]=2)[NH:45][C:44](=[O:49])[CH:43]=[CH:42]3)[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1>C(N(CC)CC)C.CN(C)C=O>[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([N:36]2[CH2:37][CH2:38][N:33]([C:39]3[CH:40]=[C:41]4[C:46](=[CH:47][CH:48]=3)[NH:45][C:44](=[O:49])[CH:43]=[CH:42]4)[CH2:34][CH2:35]2)=[O:10])[N:6]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 854632(2-methyl-1,3-thiazol-4-yl)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13236366HCID 13236366, compound

Product 1

HCID 20072843HCID 20072843, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 2-(2-methyl-4-thiazolyl)acetic acid (628 mg), 1-hydroxybenzotriazole (648 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (917 mg) and N,N-dimethylformamide (25 ml) was stirred for 1 hour at ambient temperature. 6-(1-Piperazinyl)-2(1H)-quinolinone (687 mg) and triethylamine (1 ml) were added thereto, and the mixture was stirred for 3 hours at the same temperature. After the reaction mixture was concentrated in vacuo, to the residue were added ethyl acetate (10 ml) and water (10 ml) and the mixture was stirred. The resulting oil was separated by decantation and dissolved in tetrahydrofuran. The solution was washed with brine, dried over magnesium sulfate and concentrated. The residue was subjected to a column chromatography on silica gel (80 g) and eluted with 3% solution of methanol in chloroform. The fractions containing the desired compound were collected and concentrated to give a residue, which was crystallized from ethyl acetate-diethyl ether to give 6-[4-{2-(2-methyl- 4-thiazolyl)acetyl}-1-piperazinyl]-2(1H)-quinolinone (0.74 g).

Workup

  1. stirringthe mixture was stirred for 3 hours at the same temperature
  2. concentrationAfter the reaction mixture was concentrated in vacuo, to the residue
  3. additionwere added ethyl acetate (10 ml) and water (10 ml)
  4. stirringthe mixture was stirred
  5. customThe resulting oil was separated by decantation
  6. dissolutiondissolved in tetrahydrofuran
  7. washThe solution was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. washeluted with 3% solution of methanol in chloroform
  11. additionThe fractions containing the desired compound
  12. customwere collected
  13. concentrationconcentrated
  14. customto give a residue, which
  15. customwas crystallized from ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-03f7a6728eed429d933913cab5173240
Source dataset
uspto-grants-1991_01
Patent number
US04988698

Reaction notes

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