HCID 15211974, compound → HCID 69114800, compound

HRID 855610Notes

Reaction equation

HRID 855610 reaction equation
[C:1]([C:4]1[C:5]([CH3:12])=[C:6]([C:10]#[N:11])[NH:7][C:8]=1[CH3:9])(=[O:3])[CH3:2].[CH3:13][N:14]([CH3:25])[CH:15](N(C)C)C(=O)C(C)(C)C>>[CH3:13][N:14]([CH3:25])[CH:15]=[CH:2][C:1]([C:4]1[C:5]([CH3:12])=[C:6]([C:10]#[N:11])[NH:7][C:8]=1[CH3:9])=[O:3]

Participants

3

Reactant 2

HCID 15211974HCID 15211974, compoundHCID 45086221HCID 45086221, compound

Product 1

HCID 69114800HCID 69114800, compoundYield 65%

Conditions

Temperature
75 °C

Procedure

4-Acetyl-3,5-dimethyl-1H-pyrrole-2-carbonitrile (1.38 g, 8.51 mmol) was suspended in 1,1-bis-dimethylamino-3,3-dimethyl-butan-2-one (1.3 mL) and heated at 75° C. for 42 h. The reaction mixture was evaporated to dryness and the residue was purified by SiO2 chromatography (heptane/EtOAc) to afford the title compound (1.2 g, 65%) as a pale tan solid. 1H-NMR (DMSO-d6) δ: 2.21 (s, 3H, CH3), 2.31 (s, 3H, CH3), 3.32 (s, 6H, CH3), 5.22 (d, 1H, J=12.4 Hz, CH), 7.47 (d 1H, J=12.4 Hz, CH), 11.96 (br. s, 1H, NH).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe residue was purified by SiO2 chromatography (heptane/EtOAc)

Sources & evidence

ORD record
ord-8c66708e00e34dd4b64bc1d3ddab220e
Source dataset
uspto-grants-2007_08
Patent number
US07262202B2

Reaction notes

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