Hydrochloric Acid → 4-[(2-chloro-1,3-thiazol-5-yl)methyl]-7-hydroxy-6-(7-hydroxy-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)thieno[3,2-b]pyridin-5(4H)-one

HRID 601292Notes

Reaction equation

HRID 601292 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH2:7][N:8]2[C:13](=[O:14])[C:12]([C:15]3[NH:20][C:19]4[CH:21]=[CH:22][C:23]([O:25][Si](C(C)C)(C(C)C)C(C)C)=[CH:24][C:18]=4[S:17](=[O:37])(=[O:36])[N:16]=3)=[C:11]([OH:38])[C:10]3[S:39][CH:40]=[CH:41][C:9]2=3)=[CH:5][N:6]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>O1CCCC1.O>[Cl:1][C:2]1[S:3][C:4]([CH2:7][N:8]2[C:13](=[O:14])[C:12]([C:15]3[NH:20][C:19]4[CH:21]=[CH:22][C:23]([OH:25])=[CH:24][C:18]=4[S:17](=[O:36])(=[O:37])[N:16]=3)=[C:11]([OH:38])[C:10]3[S:39][CH:40]=[CH:41][C:9]2=3)=[CH:5][N:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2724141Tetrabutylammonium FluorideHCID 136373991HCID 136373991, compound

Product 1

HCID 1363742394-[(2-chloro-1,3-thiazol-5-yl)methyl]-7-hydroxy-6-(7-hydroxy-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)thieno[3,2-b]pyridin-5(4H)-oneYield 84.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The product of Example 307D (0.235 g 0.36 mmol.) in tetrahydrofuran (10 mL) was reacted with tetrabutylamonium fluoride in tetrahydrofuran (1M, 0.43 mL) at 25° C. for 2 hours. The reaction mixture was diluted with water (50 mL) and adjusted to pH 2 with 1 M HCl and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure to give the title compound (0.15 g, 84%). MS (ESI−) m/z 493 (M−H)−. The sodium salt of the title compound was prepared according to the procedure of Example 1D. 1H NMR (300 MHz, DMSO-d6)δ ppm 5.63 (s, 2 H) 7.17 (s, 1 H) 7.20 (d, J=2.57 Hz, 1 H) 7.57 (d, J=8.82 Hz, 1 H) 7.85 (d, J=5.52 Hz, 1 H) 7.95 (s, 1 H) 8.42 (d, J=5.15 Hz, 1 H) 10.42 (s, 1 H) 13.95 (s, 1H) 15.10 (s, 1 H).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a920f40bd86f4b3ea0c3d4cfc368a23a
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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