Ammonium Chloride → HCID 66636909, compound

HRID 469260Notes

Reaction equation

HRID 469260 reaction equation
[CH:1]1([NH:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:25])[C:13]([C:22](O)=[O:23])=[C:14]4[CH2:21][CH2:20][CH2:19][CH2:18][N:15]43)=[CH:10][C:9]=2[F:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClC(OCC(C)C)=O.[BH4-].[Na+].[Cl-].[NH4+]>C(N(CC)CC)C.C1COCC1>[CH:1]1([NH:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:25])[C:13]([CH2:22][OH:23])=[C:14]4[CH2:21][CH2:20][CH2:19][CH2:18][N:15]43)=[CH:10][C:9]=2[F:26])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 66636927HCID 66636927, compound

Product 1

HCID 66636909HCID 66636909, compoundYield 50.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a 50 ml THF suspension of 1.02 g of 9-(cyclohexylamino)-8-fluoro-6-oxo-2,3,4,6-tetrahydro-1H-pyrido[1,2-a]quinoline-5-carboxylic acid were added 0.5 ml of triethylamine and 0.4 ml of isobutyl chloroformate under ice-cooling, followed by stirring under ice-cooling for 1 hour. Aqueous solution (4 ml) of 431 mg of sodium borohydride was added dropwise thereto at −78° C., followed by stirring at −15° C. for 15 minutes and under ice-cooling for 30 minute. Aqueous saturated ammonium chloride was added thereto, followed by extraction with ethyl acetate and subsequent 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 495 mg of 9-(cyclohexylamino)-8-fluoro-5-(hydroxymethyl)-1,2,3,4-tetrahydro-6H-pyrido[1,2-a]quinolin-6-one.

Workup

  1. temperaturecooling
  2. temperaturecooling for 1 hour
  3. customat −78° C.
  4. stirringby stirring at −15° C. for 15 minutes and under ice-
  5. temperaturecooling for 30 minute
  6. extractionfollowed by extraction with ethyl acetate
  7. dry with materialsubsequent 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-44dc47b661e24b15a96ea3bf46aa20cf
Source dataset
uspto-grants-2014_01
Patent number
US08629126B2

Reaction notes

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