Sodium Hydroxide → HCID 178517606, compound

HRID 899313Notes

Reaction equation

HRID 899313 reaction equation
Cl[C:2]1[C:7]2=[N:8][N:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[C:6]2[CH:5]=[CH:4][N:3]=1.[OH-:25].[Na+]>C1COCC1.Cl>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[N:9]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[C:6]2[C:7]([C:2]([OH:25])=[N:3][CH:4]=[CH:5]2)=[N:8]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21880588HCID 21880588, compound

Product 1

HCID 178517606HCID 178517606, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 7-chloro-2-(2-chlorophenyl)-3-(4-chlorophenyl)-2H-pyrazolo[3,4-c]pyridine (I-9A-1a, 420 mg, 1.12 mmol) in THF (12 ml) and 3M aqueous HCl (7.5 ml) was stirred overnight at 60° C. The reaction mixture was cooled, adjusted to pH=7.5 with 5M aqueous NaOH, and extracted into ethyl acetate. The combined organic layers were dried (Na2SO4), concentrated under reduced pressure, and then repulped from 40% ethyl acetate in isopropyl ether to give the desired product (I-9A-1a) as a colorless solid (320 mg, 80%): +ES MS (M+1) 356.3; 1H NMR (400 MHz, CD2Cl2): δ 9.64 (br s, 1H), 7.55-7.41 (m, 4H), 7.36-7.32 (m, 2H), 7.23-7.19 (m, 2H), 6.96 (dd, J=7.5, 5.8 Hz, 1H), 6.50 (d, J=7.5 Hz, 1H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted into ethyl acetate
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0e1baa4dc21f4160a26aa2673493c610
Source dataset
uspto-grants-2008_04
Patent number
US07354929B2

Reaction notes

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