Di-tert-butyl dicarbonate → Acetamide, 2-(dimethylamino)-N-(5-ethyl-1,3,4-thiadiazol-2-yl)-

HRID 594920Notes

Reaction equation

HRID 594920 reaction equation
[CH3:1][C:2]1[S:6][C:5]([NH:7][C:8]([CH2:10][N:11]([CH3:13])[CH3:12])=[O:9])=[N:4][N:3]=1.[CH3:14]C(OC(OC(OC(C)(C)C)=O)=O)(C)C>C1COCC1.O>[CH3:14][CH2:1][C:2]1[S:6][C:5]([NH:7][C:8]([CH2:10][N:11]([CH3:12])[CH3:13])=[O:9])=[N:4][N:3]=1

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 1091546Acetamide, 2-(dimethylamino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)-

Product 1

HCID 1091545Acetamide, 2-(dimethylamino)-N-(5-ethyl-1,3,4-thiadiazol-2-yl)-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of AK-1 (2.00 g, 13.1 mmol) in THF (25 mL) is added Boc2O (3.45 mL, 15.0 mmol) and TEA (3.64 mL, 26.1 mmol). The reaction mixture is stirred at rt for 18 h and then diluted with H2O and extracted with EtOAc. The organic layers are concentrated to yield AK-2.

Workup

  1. extractionextracted with EtOAc
  2. concentrationThe organic layers are concentrated

Sources & evidence

ORD record
ord-a75844ee74cb44069a064a8ea63867a5
Source dataset
uspto-grants-2016_01
Patent number
US09242989B2

Reaction notes

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