Acetic Acid → HCID 19374271, compound

HRID 128633Notes

Reaction equation

HRID 128633 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)=[CH:13][C:12]([O:25][CH2:26][CH3:27])=[C:11]([CH3:28])[N:10]=2)(=[O:5])[CH2:2][CH2:3][CH3:4].[BH4-].[Na+].C(O)(=O)C.CCOCC>C(O)C.Cl>[CH2:26]([O:25][C:12]1[CH:13]=[C:14]2[C:9](=[N:10][C:11]=1[CH3:28])[N:8]=[CH:7][C:6]([CH:1]([OH:5])[CH2:2][CH2:3][CH3:4])=[C:15]2[NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[CH3:27]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 4311764Sodium borohydrideHCID 19374280HCID 19374280, compound

Product 1

HCID 19374271HCID 19374271, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent2×

Procedure

A solution of 3-butyryl-6-ethoxy-4-(4-methoxyanilino)-7-methyl-1,8-naphthyridine (8.0 g) in absolute ethanol (200 ml) was added dropwise at 0° C. over 1 hour to a solution of sodium borohydride (2.4 g) in absolute ethanol (200 ml). The mixture was allowed to warm up to ambient temperature and stirred at this temperature for 18 hours. Glacial acetic acid was added carefully to destroy excess borohydride and the resulting mixture was concentrated under reduced pressure. The residue was dissolved in water (200 ml) and extracted with dichloromethane to give a residue which was dissolved in IMS and saturated with hydrogen chloride gas. Ether was added to induce crystallisation. The mixture was filtered to give 1-[6-ethoxy-4-(4-methoxyanilino)-7-methyl-1,8-naphthyridin-3-yl]butan-1-ol, m.p. 120°-124° C.

Workup

  1. customto destroy excess borohydride
  2. concentrationthe resulting mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in water (200 ml)
  4. extractionextracted with dichloromethane
  5. customto give a residue which
  6. customcrystallisation
  7. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-8bb348490bc343b79725d5006200f8d3
Source dataset
uspto-grants-1995_11
Patent number
US05464781

Reaction notes

Loading…