Tetrahydrofuran → potassium 2-(3-tert-butyl-4-chloro-1-methyl-1H-pyrazol-5-yl)-6-(2-chlorophenyl)-4-methoxyimidazo[4,5-c]pyridin-3-ide

HRID 570286Notes

Reaction equation

HRID 570286 reaction equation
[C:1]([C:5]1[C:9]([Cl:10])=[C:8]([C:11]2[NH:28][C:14]3[C:15]([O:26][CH3:27])=[N:16][C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[Cl:25])=[CH:18][C:13]=3[N:12]=2)[N:7]([CH3:29])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].O1CCCC1.C[O-].[K+:37]>CO>[C:1]([C:5]1[C:9]([Cl:10])=[C:8]([C:11]2[N-:28][C:14]3[C:15]([O:26][CH3:27])=[N:16][C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[Cl:25])=[CH:18][C:13]=3[N:12]=2)[N:7]([CH3:29])[N:6]=1)([CH3:4])([CH3:2])[CH3:3].[K+:37]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23664618Potassium methoxideHCID 178494021HCID 178494021, compound

Product 1

HCID 76282513potassium 2-(3-tert-butyl-4-chloro-1-methyl-1H-pyrazol-5-yl)-6-(2-chlorophenyl)-4-methoxyimidazo[4,5-c]pyridin-3-ide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 50 mL, single neck round bottom flask was charged with 2-(3-tert-butyl-4-chloro-1-methyl-1H-pyrazol-5-yl)-6-(2-chlorophenyl)-4-methoxy-3H-imidazo[4,5-c]pyridine (1.99 g, 4.27 mmol, prepared as described in Example 35 above), tetrahydrofuran (4.00 mL), and methanol (4.00 mL) to yield a solution. The solution was treated with potassium methoxide (˜25% w/w in methanol, 1.20 mL, 4.28 mmol). The resulting solution was then concentrated to yield potassium 2-(3-tert-butyl-4-chloro-1-methyl-1H-pyrazol-5-yl)-6-(2-chlorophenyl)-4-methoxyimidazo[4,5-c]pyridin-3-ide as a yellow foam. 1H NMR (DMSO-d6) δ: 7.71 (dd, J=7.6, 1.7 Hz, 1H), 7.50 (dd, J=7.9, 1.3 Hz, 1H), 7.39 (td, J=7.5, 1.2 Hz, 1H), 7.35 (s, 1H), 7.27-7.34 (m, 1H), 4.03 (s, 3H), 3.97 (s, 3H), 1.39 (s, 9H)

Workup

  1. customto yield a solution
  2. concentrationThe resulting solution was then concentrated

Sources & evidence

ORD record
ord-700ddf6652ff474f8a81b5285eef508f
Source dataset
uspto-grants-2015_05
Patent number
US09023846B2

Reaction notes

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