Dimethylformamide dimethyl acetal → HCID 86759981, compound

HRID 1795964Notes

Reaction equation

HRID 1795964 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[CH2:9]([O:11][C:12]([C:14]1[CH:15]=[CH:16][N:17]2[C:22]=1[C:21](=[O:23])[N:20]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]([CH3:31])=[N:18]2)=[O:13])C>CN(C=O)C>[CH3:9][O:11][C:12]([C:14]1[CH:15]=[CH:16][N:17]2[C:22]=1[C:21](=[O:23])[N:20]([CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]([CH:31]=[CH:3][N:4]([CH3:6])[CH3:5])=[N:18]2)=[O:13]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 69591834HCID 69591834, compound

Product 1

HCID 86759981HCID 86759981, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

Dimethylformamide dimethylacetal (0.625 ml, 4.75 mmol) was added to a solution of 3-benzyl-2-methyl-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazine-5-carboxylic acid ethyl ester (0.18 g, 0.58 mmol) in DMF (1.0 mL) with 4 Å molecular sieves and the reaction mixture was heated to 140° C. in a sealed tube for 16 h. The reaction mixture was concentrated in vacuo, diluted with EtOAc (50 ml), the organic layer washed with LiCl (10%, 3×50 mL), dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound (0.18 g, 85%): 1H NMR (CDCl3) δ 7.46 (d, 1H, J=12.44 Hz), 7.25–7.33 (m, 5H), 7.19 (m, 1H), 6.99 (m, 1H), 5.30 (s, 2H), 4.58 (d, 1H, J=12.49 Hz), 3.90 (s, 3H), 2.85 (s, 6H); MS (ESI+) 353 (M++H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with EtOAc (50 ml)
  3. washthe organic layer washed with LiCl (10%, 3×50 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ea510c0ca03c4c41b2ba735315f8b298
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

Loading…