Hydrochloric Acid → 2-(4-Chloro-phenyl)-5-(4-hydroxy-3-methoxy-phenyl)-5H-thiazolo[5,4-c]pyridin-4-one

HRID 601529Notes

Reaction equation

HRID 601529 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[C:11](=[O:36])[N:12]([C:17]4[CH:22]=[CH:21][C:20]([O:23][Si](C(C)C)(C(C)C)C(C)C)=[C:19]([O:34][CH3:35])[CH:18]=4)[CH:13]=[CH:14][C:15]=3[N:16]=2)=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].Cl>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[C:11](=[O:36])[N:12]([C:17]4[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([O:34][CH3:35])[CH:18]=4)[CH:13]=[CH:14][C:15]=3[N:16]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2724141Tetrabutylammonium FluorideHCID 575017642-(4-Chloro-phenyl)-5-(3-methoxy-4-triisopropylsilanyloxy-phenyl)-5H-thiazolo[5,4-c]pyridin-4-one

Product 1

HCID 575017652-(4-Chloro-phenyl)-5-(4-hydroxy-3-methoxy-phenyl)-5H-thiazolo[5,4-c]pyridin-4-oneYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Treat a solution of 2-(4-chloro-phenyl)-5-(3-methoxy-4-triisopropylsilanyloxy-phenyl)-5H-thiazolo[5,4-c]pyridin-4-one (0.47 g, 0.87 mmol) in THF (5.0 mL) with TBAF (1.3 mL of 1N in THF) and stir for 4 h. Acidify reaction mixture to pH 4 with 1N HCl. Filter precipitate, wash several times with water, and dry to give title compound (0.23 g, 69%). MS (ES+) 385 (M+1)+. 1H NMR (400 MHz, DMSO-d6) δ 9.33 (s, 1H), 8.11 (d, 2H, J=8.4 Hz), 7.69 (d, 1H, J=7.0 Hz), 7.62 (d, 2H, J=8.8 Hz), 7.02-6.97 (m, 2H), 6.86-6.81 (m, 2H), 3.74 (s, 3H).

Workup

  1. filtrationFilter precipitate
  2. washwash several times with water
  3. customdry

Sources & evidence

ORD record
ord-3812227d788e43759598939bc4d77695
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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