Sodium Methoxide → 4-[2-(2,2-Dimethyl-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)-1,3-thiazol-4-yl]benzonitrile

HRID 1436431Notes

Reaction equation

HRID 1436431 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([NH:14][C:15]([CH3:23])([CH3:22])/[CH:16]=[CH:17]/[C:18](OC)=[O:19])[S:12][CH:13]=2)=[CH:5][CH:4]=1)#[N:2].C[O-].[Na+]>O1CCCC1>[CH3:22][C:15]1([CH3:23])[CH:16]=[CH:17][C:18](=[O:19])[N:14]1[C:11]1[S:12][CH:13]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[N:10]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86618612Methyl (2E)-4-{[4-(4-cyanophenyl)-1,3-thiazol-2-yl]amino}-4-methylpent-2-enoate

Product 1

HCID 247386264-[2-(2,2-Dimethyl-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)-1,3-thiazol-4-yl]benzonitrileYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl (2E)-4-{[4-(4-cyanophenyl)-1,3-thiazol-2-yl]amino}-4-methylpent-2-enoate (0.15 g, 0.46 mmol), prepared in the previous step, was dissolved in tetrahydrofuran (2 mL) and sodium methoxide (53 mg, 1.0 mmol) was added. The mixture was stirred for 2 h, quenched with saturated NH4Cl, diluted with ethyl acetate, washed with H2O, brine, dried over anhydrous MgSO4, filtered and concentrated. Flash chromatography (20% acetone/hexane) afforded the title compound (0.105 g, 78%) as a white solid. HRMS: calcd for C16H13N3OS+H+, 296.08521; found (ESI, [M+H]+), 296.0867; Analytical HPLC: purity 99.0% at 210-370 nm, 9.8 min; 97.8% at 304 nm, 9.8 min; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min.

Workup

  1. customquenched with saturated NH4Cl
  2. additiondiluted with ethyl acetate
  3. washwashed with H2O, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-74801089bb2b4f53b85f4bda22796707
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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