Propionyl chloride → HCID 178460088, compound

HRID 2236856Notes

Reaction equation

HRID 2236856 reaction equation
[NH2:1][C:2]1[C:3]([OH:24])=[CH:4][C:5]([CH2:8][NH:9][CH:10]=[C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([I:21])[CH:19]=3)[C:14](=[O:22])[NH:13][C:12]2=[O:23])=[N:6][CH:7]=1.[C:25](Cl)(=[O:28])[CH2:26][CH3:27]>CC(N(C)C)=O>[OH:24][C:3]1[CH:4]=[C:5]([CH2:8][NH:9][CH:10]=[C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([I:21])[CH:19]=3)[C:14](=[O:22])[NH:13][C:12]2=[O:23])[N:6]=[CH:7][C:2]=1[NH:1][C:25](=[O:28])[CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 62324Propionyl chlorideHCID 1785080254-[[(5-amino-4-oxo-1H-pyridin-2-yl)methylamino]methylidene]-6-iodoisoquinoline-1,3-dione

Product 1

HCID 178460088HCID 178460088, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 4-{[(5-Amino-4-hydroxy-pyridin-2-ylmethyl)-amino]-methylene}-6-iodo-4H-isoquinoline-1,3-dione (332 mg, 0.761 mmole), 6 mL of dimethylacetamide is stirred, then propionyl chloride (705 mg, 7.61 mmole) is added and the reaction mixture stirred for one hour. The reaction mixture is evaporated to dryness, and then stirred overnight with a saturated aqueous sodium bicarbonate solution, the solid is filtered, washed well with water and dried to give a yellow solid, 46 mg, (11%); m.p. 210-18° C. dec; MS (ES+): m/z 492.9 (M+H).

Workup

  1. stirringthe reaction mixture stirred for one hour
  2. customThe reaction mixture is evaporated to dryness
  3. stirringstirred overnight with a saturated aqueous sodium bicarbonate solution
  4. filtrationthe solid is filtered
  5. washwashed well with water
  6. customdried
  7. customto give a yellow solid, 46 mg, (11%)

Sources & evidence

ORD record
ord-68889b8e50f54cb28af423edaacf326c
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…