Sodium Hydroxide → HCID 25007064, compound

HRID 1160509Notes

Reaction equation

HRID 1160509 reaction equation
[OH-:1].[Na+].[CH:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH:4]1[NH:13][C:14]([C:16]1[CH:17]=[N:18][N:19]([C:22]3[CH:27]=[CH:26]C(C#N)=[CH:24][CH:23]=3)[C:20]=1[CH3:21])=[O:15])[CH2:10]2.[O:30]1[CH2:35][CH2:34]OCC1>>[CH:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH:4]1[NH:13][C:14]([C:16]1[CH:17]=[N:18][N:19]([C:22]3[CH:27]=[CH:26][C:34]([C:35]([OH:30])=[O:1])=[CH:24][CH:23]=3)[C:20]=1[CH3:21])=[O:15])[CH2:10]2

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 59516150HCID 59516150, compound

Product 1

HCID 25007064HCID 25007064, compoundYield 42%

Conditions

Temperature
100 °C

Procedure

A solution of 1M sodium hydroxide (24.28 mL, 24.28 mmol) was added to a stirred suspension of N-(2-adamantyl)-1-(4-cyanophenyl)-5-methyl-pyrazole-4-carboxamide (Intermediate#66) (1.25 g, 3.47 mmol) in dioxane (25 mL). The resulting suspension was stirred at 100° C. for 7 hours. The reaction mixture was concentrated, diluted with water (40 mL) and filtered through Celite. The filtrates were acidified with 1M citric acid. The precipitate was recovered by filtration, washed with water (3×20 mL) and dried under vacuum at 50° C. The crude product was purified by preparative HPLC (Phenomenex Gemini C18 110A (axia) column, 5μ silica, 30 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% formic acid) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford 4-[4-(2-adamantylcarbamoyl)-5-methyl-pyrazol-1-yl]benzoic acid (550 mg, 42%) as a pale yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water (40 mL)
  3. filtrationfiltered through Celite
  4. filtrationThe precipitate was recovered by filtration
  5. washwashed with water (3×20 mL)
  6. customdried under vacuum at 50° C
  7. customThe crude product was purified by preparative HPLC (Phenomenex Gemini C18 110A (axia) column, 5μ silica, 30 mm diameter, 100 mm length)
  8. additionFractions containing the desired compound
  9. customwere evaporated to dryness

Sources & evidence

ORD record
ord-6c1b8e4d79e442da9020a9c5009cb856
Source dataset
uspto-grants-2010_10
Patent number
US07816391B2

Reaction notes

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