Sodium bis(trimethylsilyl)amide → HCID 68690633, compound

HRID 1157838Notes

Reaction equation

HRID 1157838 reaction equation
[C:1]([CH:3](P(OCC)(OCC)=O)[N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)#[N:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[S:35]1[CH:39]=[CH:38][N:37]=[C:36]1[CH:40]=O>C1COCC1>[C:1]([C:3]([N:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH2:8][CH2:9]1)=[CH:40][C:36]1[S:35][CH:39]=[CH:38][N:37]=1)#[N:2]

Participants

5

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 27349031,3-Thiazole-2-carbaldehydeHCID 59511160HCID 59511160, compound

Product 1

HCID 68690633HCID 68690633, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a 100 ml 3 necked round bottle flask, tert-butyl 4-(cyano(diethoxyphosphoryl)methyl)piperazine-1-carboxylate (5.0 g) was taken in dry THF (25 ml) under nitrogen. Sodium bis trimethylsilyl amide (3.0 g) was added drop wise at 0° C. and stirred for 30 min, then thiazole-2-carboxaldehyde (1.60 g) in 15 ml dry THF was added drop wise to the above reaction mixture at 0° C. Reaction mixture was stirred at room temperature for overnight. TLC was checked no starting material and the reaction mixture was quenched with saturated ammonium chloride (50 ml) and ethyl acetate was added. The organic layer was washed with brine, dried and concentrated to get crude product tert-butyl 4-(1-cyano-2-(thiazol-2-yl)vinyl)piperazine-1-carboxylate as yellow liquid.

Workup

  1. customReaction mixture
  2. stirringwas stirred at room temperature for overnight
  3. customthe reaction mixture was quenched with saturated ammonium chloride (50 ml) and ethyl acetate
  4. additionwas added
  5. washThe organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e1a0a05e9b1649f3893c931e1026f71e
Source dataset
uspto-grants-2010_10
Patent number
US07807676B2

Reaction notes

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