Sodium Hydroxide → HCID 178509411, compound

HRID 2401977Notes

Reaction equation

HRID 2401977 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[C:8]([C:27]#[N:28])=[C:9]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23]C(=O)C)[CH:18]=3)[S:10][C:11]=2[C:12]2[NH:16][CH:15]=[N:14][N:13]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1>[NH2:23][C:19]1[CH:18]=[C:17]([C:9]2[S:10][C:11]([C:12]3[NH:16][CH:15]=[N:14][N:13]=3)=[C:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:30][CH:29]=3)[C:8]=2[C:27]#[N:28])[CH:22]=[CH:21][N:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178474072N-{4-[4-(4-chlorobenzyl)-3-cyano-5-(4H-1,2,4-triazol-3-yl)-2-thienyl]pyridin-2-yl}acetamide

Product 1

HCID 178509411HCID 178509411, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-{4-[4-(4-chlorobenzyl)-3-cyano-5-(4H-1,2,4-triazol-3-yl)-2-thienyl]pyridin-2-yl}acetamide (0.020 g, 0.046 mmol) in tetrahydrofuran (5.0 mL) was added sodium hydroxide (1.0M solution in water, 2.0 mL, 2.0 mmol). The solution was stirred at room temperature for 48 hours. The mixture was extracted with ethyl acetate three times, and the combined organic extracts were then dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Column chromatography was performed to yield the title compound (0.007 g, 30%). LCMS: (FA) ES+, 393. 1H NMR (400 MHz, d6-DMSO) δ: 8.75 (s, 1H), 8.07-8.03 (m, 1H), 7.36-7.26 (m, 4H), 6.83-6.79 (m, 1H), 6.78-6.76 (m, 1H), 6.34-6.29 (m, 1H), 4.61 (s, 2H), 4.04 (s, 2H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate three times
  2. dry with materialthe combined organic extracts were then dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bae9104df33a4a4583c0812f4d7029a7
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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