Sodium Hydroxide → HCID 178490046, compound

HRID 1092005Notes

Reaction equation

HRID 1092005 reaction equation
[C:1]([C:3]1[CH:26]=[CH:25][C:6]([C:7]([NH:9][C:10]2[NH:11][N:12]=[C:13]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=3)[CH:14]=2)=[O:8])=[CH:5][CH:4]=1)#[N:2].[OH-:27].[Na+]>C(O)C.O>[CH3:24][O:23][C:19]1[CH:18]=[C:17]([CH2:16][CH2:15][C:13]2[CH:14]=[C:10]([NH:9][C:7]([C:6]3[CH:5]=[CH:4][C:3]([C:1]([NH2:2])=[O:27])=[CH:26][CH:25]=3)=[O:8])[NH:11][N:12]=2)[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178490045HCID 178490045, compound

Product 1

HCID 178490046HCID 178490046, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

4-Cyano-N-[5-[2-(3-methoxyphenyl)ethyl]-2H-pyrazol-3-yl]benzamide (Example 23) (0.2 g, 0.58 mmol) and NaOH (69 mg, 1.73 mmol) were added to a solution of ethanol/water (20 ml, 3:1) and heated at 80° C. until complete consumption of starting material was observed. Care was required as the amide further hydrolysed to the carboxylic acid. The reaction was extracted with DCM (3×50 ml), dried and the solvent was removed in vacuo to yield a white solid. This was triturated with DCM to afford a white solid (20 mg, 10%); 1H NMR (400.132 MHz, DMSO) δ 2.90 (s, 4H), 3.75 (s, 3H), 6.42 (s, 1H), 6.82-6.75 (m, 3H), 7.20 (t, 1H), 7.46 (s, 1H), 7.95 (d, 2H), 8.16-8.03 (m, 3H), 10.82 (s, 1H), 12.18 (s, 1H); MH+366.

Workup

  1. extractionThe reaction was extracted with DCM (3×50 ml)
  2. customdried
  3. customthe solvent was removed in vacuo
  4. customto yield a white solid
  5. customThis was triturated with DCM

Sources & evidence

ORD record
ord-80e37e23db94490c80c1bedf53ee5cae
Source dataset
uspto-grants-2012_03
Patent number
US08129391B2

Reaction notes

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