Sodium hydride → HCID 66636923, compound

HRID 1094213Notes

Reaction equation

HRID 1094213 reaction equation
[H-].[Na+].[C:3]([O:9][N:10]=[C:11]([NH2:38])[CH2:12][O:13][C:14]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][C:19]([NH:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=[C:20]([F:25])[CH:21]=2)[N:16]([CH:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)[CH:15]=1)(=[O:8])[CH2:4][C:5]([CH3:7])=[O:6]>C1(C)C=CC=CC=1>[CH:27]1([NH:26][C:19]2[CH:18]=[C:17]3[C:22]([C:23](=[O:24])[C:14]([O:13][CH2:12][C:11]4[NH:38][C:3](=[O:8])[O:9][N:10]=4)=[CH:15][N:16]3[CH:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:21][C:20]=2[F:25])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1.[CH:27]1([NH:26][C:19]2[CH:18]=[C:17]3[C:22]([C:23](=[O:24])[C:14]([O:13][CH2:12][C:11]4[N:38]=[C:3]([CH2:4][C:5](=[O:6])[CH3:7])[O:9][N:10]=4)=[CH:15][N:16]3[CH:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:21][C:20]=2[F:25])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 86665949HCID 86665949, compound

Product 2

HCID 66636923HCID 66636923, compoundHCID 136347660HCID 136347660, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5 ml of toluene and 41 mg of 60% sodium hydride were added to 180 mg of N′-(acetoacetyloxy)-2-{[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3yl]oxy}ethanimidamide, followed by heating under reflux for 24 hours. The solvent was evaporated under a reduced pressure, and dilute hydrochloric acid was added to the resulting residue, followed by extraction with ethyl acetate and washing with water and aqueous saturated sodium chloride. After drying over anhydrous sodium sulfate, the solvent was evaporated under a reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain 10 mg of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-3-[(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)methoxy]quinolin-4(1H)-one (Example 64) and 30 mg of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-3-{[5-(2-oxopropyl)-1,2,4-oxadiazol-3-yl]methoxy} quinolin-4(1H)-one (Example 65).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 24 hours
  3. customThe solvent was evaporated under a reduced pressure, and dilute hydrochloric acid
  4. additionwas added to the resulting residue
  5. extractionfollowed by extraction with ethyl acetate
  6. washwashing with water and aqueous saturated sodium chloride
  7. dry with materialAfter drying over anhydrous sodium sulfate
  8. customthe solvent was evaporated under a reduced pressure
  9. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e0ae322364e2475aad404f5b71ac749f
Source dataset
uspto-grants-2012_03
Patent number
US08133882B2

Reaction notes

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