HCID 10846050, compound → HCID 10058473, compound

HRID 1823962Notes

Reaction equation

HRID 1823962 reaction equation
[CH3:1][N:2]([CH3:14])[C:3](=O)[CH2:4][C:5]1[C:6]2[CH:12]=[CH:11][S:10][C:7]=2[NH:8][CH:9]=1>C1COCC1>[CH3:1][N:2]([CH2:3][CH2:4][C:5]1[C:6]2[CH:12]=[CH:11][S:10][C:7]=2[NH:8][CH:9]=1)[CH3:14]

Participants

3

Reactant 1

HCID 10846050HCID 10846050, compound

Product 1

HCID 10058473HCID 10058473, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

A stirred N,N-dimethyl-2-(6H-thieno[2,3-b]pyrrol-4-yl]acetamide (1.16 g, 6 mmol) in THF is treated with LiALH4 (18 mL of 1M solution in THF, 3 equiv.) at room temperature, stirred at 40° C. for 2 h, cooled to room temperature, quenched with aqueous NaOH and extracted with EtOAc. The extracts are combined, dried over MgSO4 and concentrated in vacuo to afford the title product as a tan oil, 0.81 g (89% yield), identified by HPLC and mass spectral analyses.

Workup

  1. temperaturecooled to room temperature
  2. customquenched with aqueous NaOH
  3. extractionextracted with EtOAc
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd3a172cbff24991a40fa2a18608b363
Source dataset
uspto-grants-2006_05
Patent number
US07041695B2

Reaction notes

Loading…