Formaldehyde → 9-Methoxy-2-(morpholinomethyl)thiazolo[5,4-c]isoquinolin-5(4H)-one

HRID 1776161Notes

Reaction equation

HRID 1776161 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:7][O:8][C:9]1[C:10]2[C:11]3[N:22]=[CH:21][S:20][C:12]=3[NH:13][C:14](=[O:19])[C:15]=2[CH:16]=[CH:17][CH:18]=1.[CH2:23]=O>>[CH3:7][O:8][C:9]1[C:10]2[C:11]3[N:22]=[C:21]([CH2:23][N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)[S:20][C:12]=3[NH:13][C:14](=[O:19])[C:15]=2[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 8083MorpholineHCID 580160499-methoxy-4H-1,3-thiazolo[5,4-c]isoquinolin-5-one

Product 1

HCID 580160649-Methoxy-2-(morpholinomethyl)thiazolo[5,4-c]isoquinolin-5(4H)-one

Procedure

Morpholine (950 μL, 0.011 mmol) was added slowly to solution of 9-methoxythiazolo[5,4-c]isoquinolin-5(4H)-one in 2.6 mL of 37% aqueous formaldehyde and the resulting reaction mixture was refluxed for 7 hours. The reaction was monitored by TLC until all starting material was consumed. After cooling to room temperature, the reaction mixture was partitioned between water and ethyl acetate, the organics were separated, washed with brine, dried over Na2SO4 and solvent was evaporated under reduced pressure to produce the title compound as a pale solid.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 7 hours
  3. customwas consumed
  4. customthe reaction mixture was partitioned between water and ethyl acetate
  5. customthe organics were separated
  6. washwashed with brine
  7. dry with materialdried over Na2SO4 and solvent
  8. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-89639ac1ddc744778b61f03a13d1d4c0
Source dataset
uspto-grants-2016_02
Patent number
US09265769B2

Reaction notes

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