Water → HCID 10115013, compound

HRID 1168494Notes

Reaction equation

HRID 1168494 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:24][N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([C:12]([NH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)=[O:13])=[C:7]2[OH:23].[C:31](N1C=CN=C1)(N1C=CN=C1)=[O:32].O>CN(C=O)C>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][NH:14][C:12]([C:8]2[C:7](=[O:23])[C:6]3[C:11]4=[C:2]([NH:1][C:31](=[O:32])[N:10]4[CH:9]=2)[CH:3]=[C:4]([CH2:24][N:25]2[CH2:26][CH2:27][O:28][CH2:29][CH2:30]2)[CH:5]=3)=[O:13])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 682631,1'-Carbonyldiimidazole2×HCID 178507700HCID 178507700, compound

Product 1

HCID 10115013HCID 10115013, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 8-amino-N-(4-chlorobenzyl)-4-hydroxy-6-(4-morpholinylmethyl)-3-quinolinecarboxamide (Preparation 3, 331 mg) and 1,1′-carbonyl diimidazole (215 mg) in DMF (2.5 mL) is heated at 80° C. for 1 h. A second portion of 1,1′-carbonyl diimidazole (167 mg) is added and heating is continued for an additional 1 h. After cooling, water (8 mL) is added and the resulting precipitate is filtered off, washed with water and dried to afford 261 mg of the title compound. Physical characteristics: M.p. 286° C. (dec); 1H NMR (300 MHz, DMSO-d6) δ2.39, 3.57, 3.62, 4.57, 7.39, 7.61, 8.88, 10.0, 12.0. Anal. Found: C, 60.37; H, 4.78; N, 12.49.

Workup

  1. temperatureheating
  2. temperatureAfter cooling
  3. filtrationthe resulting precipitate is filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-2c35cb58873448219c82dd948d876bd5
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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