Dimethylamine → HCID 18405246, compound

HRID 1017734Notes

Reaction equation

HRID 1017734 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:5][N:6]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][C:8]2[O:15][C:16]([CH:18]=O)=[CH:17][C:7]1=2.C([O-])(=O)C.[Na+].[O-]S([O-])(=O)=O.[Mg+2].[CH3:35][NH:36][CH3:37].C([BH3-])#N.[Na+]>CO.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:5][N:6]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][C:8]2[O:15][C:16]([CH2:18][N:36]([CH3:37])[CH3:35])=[CH:17][C:7]1=2

Participants

8

Reactant 5

HCID 674Dimethylamine2×HCID 24083Sulfuric acid magnesium salt (1:1)HCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 18405228HCID 18405228, compound

Product 1

HCID 18405246HCID 18405246, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-(3,4-dichlorobenzyl)-2-formylfuro[3,2-b]pyrrole-5-carboxylate (0.25 g) was dissolved in methanol (5 mL) and THF (10 mL), and to this was added sodium acetate (116 mg) and a portion of MgSO4, followed by dimethylamine solution (2M in methanol, 0.53 mL). After 1 hour, a further 2.5 ml dimethylamine solution was added, followed after 30 min by sodium cyanoborohydride (0.45 g). The reaction was stirred for 18 hours and then quenched by addition of 1M potassium carbonate solution, and extracted with ethyl acetate. Combined organic extracts were dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography using ethyl acetate increasing to 10% methanol: ethyl acetate as eluent to give a yellow oil (0.15 g, 55%), NMR d(CDCl3) 2.3 (6H, s), 3.5 (2H, s), 3.8 (3H, s), 5.55 (2H, s), 6.15 (1H, s), 6.85 (1H, s), 6.95 (2H, dd), 7.2 (1H, d), 7.35 (1H, d). M/z (+) 383 (MH+), 381, 338, 336.

Workup

  1. customquenched by addition of 1M potassium carbonate solution
  2. extractionextracted with ethyl acetate
  3. dry with materialCombined organic extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-343df31110ac4b5f960d678d591b4197
Source dataset
uspto-grants-2002_11
Patent number
US06479527B1

Reaction notes

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