Tetrahydrofuran → HCID 69507344, compound

HRID 1623103Notes

Reaction equation

HRID 1623103 reaction equation
[CH3:1][Mg]I.N[C:5]1[C:14]2[N:15]=[C:16]([CH2:27][CH2:28][CH2:29][CH3:30])[N:17](CCCC(N(OC)C)=O)[C:13]=2[C:12]2[N:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:6]=1.[O:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1>>[CH2:27]([C:16]1[N:15]([CH2:35][CH2:34][CH2:33][C:32](=[O:31])[CH3:1])[C:14]2[C:5]3[N:6]=[CH:7][CH:8]=[CH:9][C:10]=3[N:11]=[CH:12][C:13]=2[N:17]=1)[CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 86612246HCID 86612246, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 69507344HCID 69507344, compound

Procedure

Methylmagnesium iodide (3M solution in tetrahydrofuran, 5.6 mL, 16.9 mmol, 1.5 eq) was added dropwise over 10 minutes to a chilled (0°) solution of 4-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-N-methoxy-N-methylbutanamide (4.0 g, 11.25 mmol, 1 eq) in tetrahydrofuran (THF) (50 mL). The reaction mixture was stirred at ambient temperature for 4 hours, quenched with 1 M hydrochloric acid, and concentrated under reduced pressure. The residue was diluted with dichloromethane (75 mL) and saturated aqueous sodium bicarbonate (50 mL). The aqueous layer was extracted with dichloromethane (2×30 mL) and the combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to produce 3.12 g of 5-(2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)pentan-2-one as a tan solid.

Workup

  1. customquenched with 1 M hydrochloric acid
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with dichloromethane (75 mL) and saturated aqueous sodium bicarbonate (50 mL)
  4. extractionThe aqueous layer was extracted with dichloromethane (2×30 mL)
  5. dry with materialthe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-230db3dc3605431eb761c778fc29b0ec
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

Loading…