Sodium Hydroxide → HCID 59375647, compound

HRID 2193020Notes

Reaction equation

HRID 2193020 reaction equation
[C:1]([NH:4][NH:5][C:6]([C:8]1[CH:25]=[CH:24][C:11]2[C:12]([CH:21]([CH3:23])[CH3:22])=[N:13][C:14]3[CH:15]=[CH:16][NH:17][C:18](=O)[C:19]=3[C:10]=2[CH:9]=1)=O)(=[O:3])[CH3:2].O=P(Cl)(Cl)[Cl:28].[OH-].[Na+]>C(#N)C>[Cl:28][C:18]1[N:17]=[CH:16][CH:15]=[C:14]2[C:19]=1[C:10]1[CH:9]=[C:8]([C:6]3[O:3][C:1]([CH3:2])=[N:4][N:5]=3)[CH:25]=[CH:24][C:11]=1[C:12]([CH:21]([CH3:22])[CH3:23])=[N:13]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 59375665HCID 59375665, compound

Product 1

HCID 59375647HCID 59375647, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
100 °C

Procedure

To a stirred suspension of N′-acetyl-6-isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridine-9-carbohydrazide (30 mg, 0.089 mmol) in ACN (1.0 mL) was added POCl3 (1.0 ml). The resulting suspension was stirred at 100° C. in a sealed vial for 3 hr. The solution was diluted with additional acetonitrile (10 mL), and then added to cooled 6N NaOH (20 mL). The resulting mixture was extracted with EtOAc (1×25 mL). The organic layer was dried over sodium sulfate, filtered and concentrated to afford crude 1-chloro-6-isopropyl-9-(5-methyl-1,3,4-oxadiazol-2-yl)benzo[c]-1,6-naphthyridine that was used directly without further purification. LRMS (ESI) calc'd for (C18H15ClN4O) [M+H]+, 339.1; found 339.1.

Workup

  1. additionadded
  2. extractionThe resulting mixture was extracted with EtOAc (1×25 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e6e482549d324056b12062fb13418f61
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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