Sodium hydride → HCID 24957317, compound

HRID 1097776Notes

Reaction equation

HRID 1097776 reaction equation
[OH:1][NH:2][C:3](=[NH:5])[CH3:4].[H-].[Na+].CO[C:10]([C:12]1[N:13]([CH:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][C:19](=[O:27])[C:18]2([CH3:29])[CH3:28])[CH:14]=[N:15][CH:16]=1)=O>C1COCC1>[CH3:28][C:18]1([CH3:29])[CH:17]([N:13]2[C:12]([C:10]3[O:1][N:2]=[C:3]([CH3:4])[N:5]=3)=[CH:16][N:15]=[CH:14]2)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][C:19]1=[O:27]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 24962820HCID 24962820, compoundHCID 178465666HCID 178465666, compound

Product 1

HCID 24957317HCID 24957317, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-hydroxy-acetamidine (62 mg, 0.84 mmol) is added to a suspension of 3 Å molecular sieves in anhydrous THF (2 mL). After 20 min, NaH (60% in oil, 37 mg, 0.92 mmol) is added. The resulting suspension is stirred for 40 min and a solution of 3-(3,3-Dimethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-4-yl)-3H-imidazole-4-carboxylic acid methyl ester (100 mg, 0.34 mmol) in THF (dry, 1 mL) is added. The resulting mixture is refluxed for 1 h. The solvent is removed under vacuum and the residue is purified by silca gel chromatography (mobile phase 0 to 40% ethyl acetate-heptane v/v), and gives the title compound (74 mg).

Workup

  1. temperatureThe resulting mixture is refluxed for 1 h
  2. customThe solvent is removed under vacuum
  3. customthe residue is purified by silca gel chromatography (mobile phase 0 to 40% ethyl acetate-heptane v/v)

Sources & evidence

ORD record
ord-56d8b2f406d94b408201ec567409ed99
Source dataset
uspto-grants-2012_03
Patent number
US08143278B2

Reaction notes

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