Pyridine → HCID 13885773, compound

HRID 580010Notes

Reaction equation

HRID 580010 reaction equation
[CH:1]([O:4][C:5]1[N:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:8]([C:16]([O:18][CH3:19])=[O:17])=[C:9]([CH3:15])[NH:10]2)([CH3:3])[CH3:2].N1C=CC=CC=1.C1C=C[NH+]=CC=1.Br[Br-]Br.[CH3:41][N:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1>C(O)C.C(Cl)(Cl)Cl>[CH:1]([O:4][C:5]1[N:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:8]([C:16]([O:18][CH3:19])=[O:17])=[C:9]([CH2:15][N:45]1[CH2:46][CH2:47][N:42]([CH3:41])[CH2:43][CH2:44]1)[NH:10]2)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 531671-MethylpiperazineHCID 13603466HCID 13603466, compound

Product 1

HCID 13885773HCID 13885773, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
-10 °C

Procedure

1.0 g (3.0 mMole) methyl (±)-1,4-dihydro-5-isopropoxy-2-methyl-4-phenyl-1,6-naphthyridine-3-carboxylate (for the preparation cf. Federal Republic of Germany Patent Specification No. 34 31 303) in ethanol-free chloroform is cooled to -10° C., mixed with 0.26 ml (3.2 mMole) pyridine and subsequently portionwise with 1.1 g (3.1 mMole) pyridinium bromide perbromide (90%). After 30 minutes at -10° C., 0.62 g (6.2 mMole) N-methylpiperazine is added dropwise thereto and the reaction mixture is stirred for 15 minutes at -10° C. and then warmed to 20° C. within the course of one hour. The reaction mixture is diluted with chloroform, washed with water and the organic phase is dried over anhydrous sodium sulphate. The residue obtained after distilling off the solvent is chromatographed on silica gel with dichloromethane/methanol (9:1 v/v). The fraction with the Rf of 0.3 is recrystallized from n-hexane. There is obtained methyl (±)-1,4-dihydro-5 -isopropoxy-2-[(4-methyl-piperazin-l-yl)-methyl]-4-phenyl-1,6-naphthyridine-3-carboxylate in the form of colorless crystals; mp 149°-151° C.

Workup

  1. temperaturewarmed to 20° C. within the course of one hour
  2. washwashed with water
  3. dry with materialthe organic phase is dried over anhydrous sodium sulphate
  4. customThe residue obtained
  5. distillationafter distilling off the solvent
  6. customis chromatographed on silica gel with dichloromethane/methanol (9:1 v/v)
  7. customThe fraction with the Rf of 0.3 is recrystallized from n-hexane

Sources & evidence

ORD record
ord-6d6466f8b2fb4c0992689456f6b874fc
Source dataset
uspto-grants-1988_06
Patent number
US04751228

Reaction notes

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