Hydrochloric Acid → HCID 67059755, compound

HRID 1671295Notes

Reaction equation

HRID 1671295 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([C:17]3[S:18][CH:19]=[C:20]([C:22]([O:24]CC)=[O:23])[N:21]=3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:5]2=[CH:4][CH:3]=1.[OH-].[Na+].Cl.[CH2:30]([OH:32])[CH3:31]>>[CH2:30]([O:32][C:2]1[N:7]=[C:6]2[N:8]([C:17]3[S:18][CH:19]=[C:20]([C:22]([OH:24])=[O:23])[N:21]=3)[N:9]=[C:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:5]2=[CH:4][CH:3]=1)[CH3:31]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 59179910HCID 59179910, compound

Product 1

HCID 67059755HCID 67059755, compound

Procedure

To an ethanol (2 mL, manufactured by Wako Pure Chemical Industries, Ltd.) solution of ethyl 2-(6-chloro-3-phenyl-1H-pyrazolo[3,4-b]pyridin-1-yl)thiazole-4-carboxylate (33 mg), which had been synthesized from the compound of Reference Example 33 according to the method of Example 3, 5 M sodium hydroxide (500 μL, manufactured by Kanto Chemical Co., Inc.) was added, and the mixture was stirred for one hour at room temperature. 5 M hydrochloric acid (500 μL, manufactured by Kanto Chemical Co., Inc.) was added to neutralize the mixture, and then the mixture was extracted with chloroform (3×3 mL), washed with brine (3 mL), and dried (MgSO4). The solvent was then evaporated, to give 17.6 mg of the title compound. LC-MS: HPLC retention time 1.38 minutes, m/z (M+H) 367, condition C-1.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with chloroform (3×3 mL)
  3. washwashed with brine (3 mL)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-d6b1c5c6ab94492fbed2bb137c129b1b
Source dataset
uspto-grants-2011_08
Patent number
US07994202B2

Reaction notes

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