Trifluoroacetic acid → 5-[4-(azetidin-3-yloxy)-3-methoxy-phenyl]-2-(4-chloro-phenyl)-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one

HRID 554870Notes

Reaction equation

HRID 554870 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][C:22]4[N:25]=[C:26]([C:28]5[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=5)[S:27][C:21]=4[C:20]3=[O:35])=[CH:15][C:14]=2[O:36][CH3:37])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)Cl>[NH:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][C:22]4[N:25]=[C:26]([C:28]5[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=5)[S:27][C:21]=4[C:20]3=[O:35])=[CH:15][C:14]=2[O:36][CH3:37])[CH2:9]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 59238512HCID 59238512, compound

Product 1

HCID 249911625-[4-(azetidin-3-yloxy)-3-methoxy-phenyl]-2-(4-chloro-phenyl)-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-oneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 3-{4-[2-(4-chloro-phenyl)-4-oxo-6,7-dihydro-4H-thiazolo[5,4-c]pyridin-5-yl]-2-methoxy-phenoxy}-azetidine-1-carboxylic acid tert-butyl ester (2.71 g, 5.00 mmol) in CH2Cl2 (20 mL). Add trifluoroacetic acid (5.88 mL, 77.79 mmol). Stir at room temperature for one hour and then add 5 N NaOH to pH=8-10. Collect a white/yellow precipitate via vacuum filtration, and wash the solid with EtOAc followed by Et2O. Dry the solid overnight in vacuo at about 50° C. to give 2.21 g (>99%) of the title compound. ES/MS m/z (35Cl) 442.0 [M+1]+.

Workup

  1. customCollect a white/yellow precipitate
  2. filtrationvia vacuum filtration
  3. washwash the solid with EtOAc
  4. customDry the solid overnight in vacuo at about 50° C.

Sources & evidence

ORD record
ord-838820d950c443be9ec08502cc459808
Source dataset
uspto-grants-2011_11
Patent number
US08049013B2

Reaction notes

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