Fumaric Acid → 2-(4-Chloro-phenyl)-5-[3-methoxy-4-(1-methyl-azetidin-3-yloxy)-phenyl]-5H-thiazolo[5,4-c]pyridin-4-one, fumarate salt

HRID 554849Notes

Reaction equation

HRID 554849 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[C:11](=[O:31])[N:12]([C:17]4[CH:22]=[CH:21][C:20]([O:23][CH:24]5[CH2:27][N:26]([CH3:28])[CH2:25]5)=[C:19]([O:29][CH3:30])[CH:18]=4)[CH:13]=[CH:14][C:15]=3[N:16]=2)=[CH:4][CH:3]=1.[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]/[C:35]([OH:37])=[O:36]>O1CCOCC1>[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]/[C:35]([OH:37])=[O:36].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[C:11](=[O:31])[N:12]([C:17]4[CH:22]=[CH:21][C:20]([O:23][CH:24]5[CH2:25][N:26]([CH3:28])[CH2:27]5)=[C:19]([O:29][CH3:30])[CH:18]=4)[CH:13]=[CH:14][C:15]=3[N:16]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 249907962-(4-Chloro-phenyl)-5-[3-methoxy-4-(1-methyl-azetidin-3-yloxy)-phenyl]-5H-thiazolo[5,4-c]pyridin-4-one

Product 1

HCID 1317292502-(4-Chloro-phenyl)-5-[3-methoxy-4-(1-methyl-azetidin-3-yloxy)-phenyl]-5H-thiazolo[5,4-c]pyridin-4-one, fumarate saltYield 62.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Dissolve 2-(4-chloro-phenyl)-5-[3-methoxy-4-(1-methyl-azetidin-3-yloxy)-phenyl]-5H-thiazolo[5,4-c]pyridin-4-one (638 mg, 1.41 mmol) in 1,4-dioxane at 100° C. To the above solution, add a solution of fumaric acid (5.64 mL, 1.41 mmol, 0.25 M in water). Stir the resulting solution at 100° C. for 5 min, then at 50° C. for one hour. Concentrate the solution with a stream of nitrogen gas to ¾ volume. Warm the mixture up to 100° C. until all the solids dissolve, then slowly cool to −10° C. Collect the white precipitate by filtration and wash the solids with cold dioxane (10 mL). Dry the solid at room temperature over the weekend to obtain 500 mg (62%) of the title compound as a fine white powder. ES/MS m/z (35Cl) 454 [M+1]+.

Workup

  1. waitat 50° C. for one hour
  2. concentrationConcentrate the solution with a stream of nitrogen gas
  3. temperatureWarm the mixture up to 100° C. until all the solids
  4. dissolutiondissolve
  5. temperatureslowly cool to −10° C
  6. customCollect the white precipitate
  7. filtrationby filtration
  8. washwash the solids with cold dioxane (10 mL)
  9. customDry the solid at room temperature over the weekend

Sources & evidence

ORD record
ord-82a36edd35b34a98b72440995f773142
Source dataset
uspto-grants-2011_11
Patent number
US08049013B2

Reaction notes

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