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Sodium bis(trimethylsilyl)amide → 4-[2-(2,2-Dimethyl-5-oxopyrrolidin-1-yl)-1,3-thiazol-4-yl]benzonitrile

HRID 1436433
Notes
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Reaction equation

HRID 1436433 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])[CH2:16][CH2:17][C:18](OC)=[O:19])[S:12][CH:13]=2)=[CH:5][CH:4]=1)#[N:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>O1CCCC1>[CH3:22][C:15]1([CH3:23])[CH2:16][CH2:17][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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 86618613Methyl 4-{[4-(4-cyanophenyl)-1,3-thiazol-2-yl]amino}-4-methylpentanoate

Product 1

HCID 689027704-[2-(2,2-Dimethyl-5-oxopyrrolidin-1-yl)-1,3-thiazol-4-yl]benzonitrileYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Methyl 4-{[4-(4-cyanophenyl)-1,3-thiazol-2-yl]amino}-4-methylpentanoate (0.31 g, 0.94 mmol), prepared in the previous step, was dissolved in tetrahydrofuran (18 mL) and sodium bis(trimethylsilyl)amide (1M in tetrahydrofuran, 0.94 mL, 0.94 mmol) was added. The mixture was stirred at 25° C. for 2 h. The reaction was 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 (0.27 g, 97%) as a white solid. HRMS: calcd for C16H15N3OS+H+, 298.10086; found (ESI, [M+H]+), 298.1; Analytical HPLC: purity 94.8% at 210-370 nm, 9.9 min; 98.2% at 244 nm, 9.9 min; the Xterra® RP18 column, 3.5%, 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. customThe reaction was quenched 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-52f914fa57114e98adcfef46eebedd64
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07618990B2

Reaction notes

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