Sodium Hydroxide → HCID 178517606, compound

HRID 915851Notes

Reaction equation

HRID 915851 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+]>Cl.O1CCCC1>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[N:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[N:8]=[C:7]3[C:6]=2[CH:5]=[CH:4][N:3]=[C:2]3[OH:25])=[CH:12][CH:13]=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
45 °C

Procedure

A stirred mixture of 7-chloro-3-(4-chlorophenyl)-2-(2-chlorophenyl)-2H-pyrazolo[3,4-c]pyridine (I-1A-6a; 420 mg, 1.12 mmol) in 3M aqueous HCl (7.5 ml) and tetrahydrofuran (12 ml) was heated overnight at 45° C. The reaction mixture was cooled and the pH adjusted to 8 with 5M aqueous NaOH. The aqueous layer was dried (Na2SO4), concentrated, in vacuo, and the resulting solid repulped from 40% ethyl acetate/isopropyl ether (20 ml) to afford I-10A-14a as an off-white solid (320 mg, 80%): +ESI MS (M+1) 356.3; 1H NMR (400 MHz, CD2Cl2) δ 9.64 (br s, 1H), 7.55-7.41 (m, 4H), 7.34 (d, J=8.7 Hz, 2H), 7.21 (d, J=8.7 Hz, 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. dry with materialThe aqueous layer was dried (Na2SO4)
  3. concentrationconcentrated, in vacuo

Sources & evidence

ORD record
ord-90f5312162cd467eb6f82e5e78ef9e1a
Source dataset
uspto-grants-2007_09
Patent number
US07268133B2

Reaction notes

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