1,1,1-Trimethoxybutane → HCID 57455398, compound

HRID 1623143Notes

Reaction equation

HRID 1623143 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:9][CH:8]=[CH:7][CH:6]=2.[C:21](OC)(OC)(OC)[CH2:22][CH2:23][CH3:24]>C1(C)C=CC=CC=1.Cl.N1C=CC=CC=1>[CH2:22]([C:21]1[N:12]([CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:11]2[C:10]3[N:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1)[CH2:23][CH3:24]

Participants

5

Reactant 2

HCID 1235121,1,1-TrimethoxybutaneHCID 57455388HCID 57455388, compound2×

Product 1

HCID 57455398HCID 57455398, compound

Reagents, catalysts & solvents 2

HCID 10176127Pyridinium chlorideCatalystHCID 1140TolueneSolvent

Procedure

The preparation of ethyl 4-[(3-amino[1,5]naphthyridine-4-yl)amino]butyrate is described in Parts A-B of Example 4. Trimethyl orthobutyrate (9.1 mL, 57.2 mmol) and pyridine hydrochloride (110 mg, 0.95 mmol) were added to a solution of ethyl 4-[(3-amino-[1,5]naphthyridine-4-yl)amino]butyrate (13.08 g, 47.7 mmol) in toluene (190 mL) and heated at reflux for 3 hours. The reaction mixture was cooled to ambient temperature and concentrated under reduced pressure. The residue was dissolved in dichloromethane (200 mL) and washed with saturated aqueous sodium bicarbonate (150 mL). The aqueous layer was extracted with dichloromethane (2×50 mL). The combined organics were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 14.9 g of ethyl 4-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-butyrate as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane (200 mL)
  5. washwashed with saturated aqueous sodium bicarbonate (150 mL)
  6. extractionThe aqueous layer was extracted with dichloromethane (2×50 mL)
  7. dry with materialThe combined organics were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b3a7a4da6f9a485eb6bd85efc06f8003
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

Loading…