Hydrochloric Acid → HCID 68596222, compound

HRID 1943204Notes

Reaction equation

HRID 1943204 reaction equation
[N:1]([C:4]1([CH3:25])[CH2:9][CH2:8][N:7]([CH2:10][C@H:11]2[N:21]3[C:22]4[N:13]([C:14](=[O:24])[CH2:15][CH2:16][C:17]=4[CH:18]=[CH:19][C:20]3=[O:23])[CH2:12]2)[CH2:6][CH2:5]1)=C=O.[OH-].[Na+].Cl>C1COCC1.O>[NH2:1][C:4]1([CH3:25])[CH2:5][CH2:6][N:7]([CH2:10][C@H:11]2[N:21]3[C:22]4[N:13]([C:14](=[O:24])[CH2:15][CH2:16][C:17]=4[CH:18]=[CH:19][C:20]3=[O:23])[CH2:12]2)[CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86642103HCID 86642103, compound

Product 1

HCID 68596222HCID 68596222, compoundYield 132.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (1R)-1-[(4-isocyanato-4-methyl-1-piperidinyl)methyl]-1,2,5,6-tetrahydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione (561 mg, 1.638 mmol) in THF (10 ml) and water (10.00 ml) at rt was treated with sodium hydroxide (5 ml, 10.00 mmol), and stirred at rt for 1 h. Reaction was then treated with concentrated HCl (5 ml, 12M) and stirred at rt for 18 h, then evaporated. The resultant solid was treated with methanol (20 ml) and then the solvent was decanted from the solid and evaporated to give the product as an impure green solid (687 mg, 108%).

Workup

  1. customReaction
  2. stirringstirred at rt for 18 h
  3. customevaporated
  4. additionThe resultant solid was treated with methanol (20 ml)
  5. customthe solvent was decanted from the solid
  6. customevaporated

Sources & evidence

ORD record
ord-2436433de56e4fdfbbd313976501ec78
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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