Hydrochloric Acid → 5-[4-(Azetidin-3-yloxy)-3-methoxy-phenyl]-2-(4-chloro-phenyl)-5H-thiazolo[5,4-c]pyridin-4-one, hydrochloride salt

HRID 554844Notes

Reaction equation

HRID 554844 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]3[S:26][C:25]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)=[N:24][C:23]=3[CH2:34][CH:35](OC)OC)=[O:21])=[CH:15][C:14]=2[O:40][CH3:41])[CH2:9]1)=O)(C)(C)C.Cl>CCO>[ClH:33].[NH:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH:35]=[CH:34][C:23]4[N:24]=[C:25]([C:27]5[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=5)[S:26][C:22]=4[C:20]3=[O:21])=[CH:15][C:14]=2[O:40][CH3:41])[CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 674612343-(4-{[2-(4-Chloro-phenyl)-4-(2,2-dimethoxy-ethyl)-thiazole-5-carbonyl]-amino}-2-methoxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 1317292485-[4-(Azetidin-3-yloxy)-3-methoxy-phenyl]-2-(4-chloro-phenyl)-5H-thiazolo[5,4-c]pyridin-4-one, hydrochloride saltYield 194.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Mix 3-(4-{[2-(4-chloro-phenyl)-4-(2,2-dimethoxy-ethyl)-thiazole-5-carbonyl]-amino}-2-methoxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester (208 g, 344 mmol) in EtOH (2.2 L) and treat with concentrated HCl (208 mL). Heat the mixture to reflux for one hour and then cool to 0° C. Collect the solid by filtration and rinse with ice-cold Et2O (4×500 mL). Dry the solid under vacuum at 55° C. for 2 days to give 159 g (97%) of the title compound as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ: 9.37 (s, 2H), 8.15 (m, 2H), 7.75 (d, 1H, J=7.6), 7.66 (m, 2H), 7.22 (d, 1H, J=7.5), 7.05 (d, 1H, J=7.3), 7.01 (dd, 1H, J=2.5, 8.7), 6.92 (d, 1H, J=8.6), 5.09 (m, 1H), 4.45 (m, 2H), 4.04 (m, 2H), 3.82 (s, 3H).

Workup

  1. temperatureHeat the mixture
  2. temperatureto reflux for one hour
  3. customCollect the solid
  4. filtrationby filtration
  5. washrinse with ice-cold Et2O (4×500 mL)
  6. customDry the solid under vacuum at 55° C. for 2 days

Sources & evidence

ORD record
ord-f6ccfbc159d54bbea346bcd2f4cc3371
Source dataset
uspto-grants-2011_11
Patent number
US08049013B2

Reaction notes

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