Potassium Hydroxide → HCID 57635767, compound

HRID 2109951Notes

Reaction equation

HRID 2109951 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]2[C:12]([C:17]([OH:19])=[O:18])=[N:13][CH:14]=[CH:15][CH:16]=2)[N:7]([C:20]2[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:27])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.[Cl:32]CCl.ClN1C(=O)CCC1=O.[OH-].[K+]>O>[C:1]([C:5]1[C:9]([Cl:32])=[C:8]([NH:10][C:11]2[C:12]([C:17]([OH:19])=[O:18])=[N:13][CH:14]=[CH:15][CH:16]=2)[N:7]([C:20]2[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:27])[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 31398ChlorosuccinimideHCID 11257045HCID 11257045, compoundHCID 21922555Acetic acid methylene chloride

Product 1

HCID 57635767HCID 57635767, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-{[3-tert-butyl-1-(2,6-dimethylphenyl)-1H-pyrazol-5-yl]amino}pyridine-2-carboxylic acid (Example 10, 50 mg, 0.14 mmol) in an acetic acid/dichloromethane mixture (1 mL of each) was added N-chlorosuccinimide (18 mg, 0.14 mmol). The solution was stirred at rt for 12 h, and then water (10 mL) was added. The reaction mixture was basified to pH 9 using KOH (1.0 M ice cold solution). The water layer was extracted with dichloromethane (50 mL), and the organic phase was subsequently washed with saturated sodium sulfite, brine, and concentrated to dryness. The crude material was subjected to HPLC purification to give the desired product (42 mg, 76%). 1H NMR (300 MHz, CD2Cl2) δ 10.45 (s, 1H), 9.30 (s, 1H), 8.04 (d, 1H), 7.50 (m, 1H), 7.25 (m, 2H), 7.15 (m, 2H), 2.02 (s, 6H), 1.43 (s, 9H). ES-MS m/z 399.0 (MH+); HPLC RT (min) 3.33.

Workup

  1. extractionThe water layer was extracted with dichloromethane (50 mL)
  2. washthe organic phase was subsequently washed with saturated sodium sulfite, brine
  3. concentrationconcentrated to dryness
  4. customThe crude material was subjected to HPLC purification

Sources & evidence

ORD record
ord-e0a60727b7164c3bae5bf1246ef44b2a
Source dataset
uspto-grants-2009_04
Patent number
US07517878B2

Reaction notes

Loading…