HCID 10846050, compound → HCID 10058473, compound

HRID 1352233Notes

Reaction equation

HRID 1352233 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 MgSO4and 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. customdried over MgSO4and
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa529ad859c5444ea45e54641795163b
Source dataset
uspto-grants-2007_05
Patent number
US07220756B2

Reaction notes

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