Hydrochloric Acid → 2-(4-Chloro-phenyl)-5-[3-methoxy-4-(1-methyl-azetidin-3-yloxy)-phenyl]-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one, hydrochloride salt

HRID 554873Notes

Reaction equation

HRID 554873 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)[CH2:13][CH2:14][C:15]=3[N:16]=2)=[CH:4][CH:3]=1.Cl.C(OCC)C>C(Cl)Cl>[ClH:1].[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)[CH2:13][CH2:14][C:15]=3[N:16]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 24991163HCID 24991163, compound

Product 1

HCID 1317292552-(4-Chloro-phenyl)-5-[3-methoxy-4-(1-methyl-azetidin-3-yloxy)-phenyl]-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one, hydrochloride saltYield 183.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 2-(4-chloro-phenyl)-5-[3-methoxy-4-(1-methyl-azetidin-3-yloxy)-phenyl]-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one (2.1 g, 4.6 mmol) in CH2Cl2 (25 mL) and treat with 4.0 M HCl (1.3 mL, 5.2 mmol, solution in diethyl ether). Stir the solution for 10 min. Add additional diethyl ether (25 mL) and isolate the precipitate by filtration. Wash the solid with diethyl ether and dry under vacuum to give 2.08 g (92%) of the title compound. ES/MS m/z (35Cl) 456 [M+1]+.

Workup

  1. customisolate the precipitate
  2. filtrationby filtration
  3. washWash the solid with diethyl ether
  4. customdry under vacuum

Sources & evidence

ORD record
ord-5e7f9f91410c425cb2ab15fb88f5f4e5
Source dataset
uspto-grants-2011_11
Patent number
US08049013B2

Reaction notes

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