Water → HCID 58032142, compound

HRID 2167261Notes

Reaction equation

HRID 2167261 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([NH:16][NH2:17])=[O:15])=[CH:11][CH:12]=2)[CH:7]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[CH:21][CH:20]=2)[CH2:6][CH:5]1[CH3:31])(=[O:3])[CH3:2].C(N(CC)CC)C.O.[O:40]1CCC[CH2:41]1>>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[O:15][C:41](=[O:40])[NH:17][N:16]=3)=[CH:11][CH:12]=2)[CH:7]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([N:25]3[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)=[CH:23][CH:24]=2)[CH2:6][CH:5]1[CH3:31])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 58032165HCID 58032165, compound2×

Product 1

HCID 58032142HCID 58032142, compound

Procedure

72 mg of 1-acetyl-4-[(4-morpholinophenyl)amino]-2-methyl-1,2,3,4-tetrahydroquinoline-6-carbohydrazide (compound 133) was dissolved in 4 mL of tetrahydrofuran, and 55 mg of N,N′-carbonyldiimidazole and 47 μL of triethylamine were added to the solution. The mixture was stirred overnight at room temperature. After completion of the reaction, water was added to the mixture, and the mixture was extracted three times with chloroform. The extraction product was washed with saturated brine, dehydrated over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by using silica gel chromatography (ethyl acetate:hexane=5:1), and thus 57 mg (cis:trans=4:1, 75%) of the title compound was obtained as a pale green powder.

Workup

  1. additionwas added to the mixture
  2. extractionthe mixture was extracted three times with chloroform
  3. washThe extraction product was washed with saturated brine
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified
  6. customwas obtained as a pale green powder

Sources & evidence

ORD record
ord-1e04907f9d304b5c9677b95aab4cd859
Source dataset
uspto-grants-2015_06
Patent number
US09045423B2

Reaction notes

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