Acetaldehyde → HCID 10268158, compound

HRID 2216640Notes

Reaction equation

HRID 2216640 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].C(=O)C.C(N(CC)CC)C.[CH3:18][C:19]1[CH:23]=[C:22]([CH3:24])[NH:21][C:20]=1[CH:25]=[C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][C:27]1=[O:35]>CN(C=O)C>[C:5]([O:4][CH:1]([N:28]1[C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)/[C:26](=[CH:25]/[C:20]2[NH:21][C:22]([CH3:24])=[CH:23][C:19]=2[CH3:18])/[C:27]1=[O:35])[CH3:2])(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 123015Semaxinib

Product 1

HCID 10268158HCID 10268158, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of acetic anhydride (2.1 g, 20 mmol), acetaldehyde (4.4 g, 100 mmol), triethylamine (2.0 g, 20 mmol) and 3-(3,5-dimethyl-1H-pyrrol-2-ylmethylidene)-1,3-dihydro-indol-2-one (2.38 g, 10 mmol) in DMF (30 mL) was stirred at room temperature for 3 days. The solvents were removed and the residual oil was chromatographed on silica gel to give, as the first product eluted from the column, 2.5 g of product, which was crystallized from ether to give 2.1 g of the title compound, mp 107–110° C. HPLC Rt 6.78 min. 1H NMR (CDCl3) δ 1.81 (d, 3H), 2.09 (s, 3H), 2.33 (s, 3H), 2.38 (s, 3H), 5.98 (s, 2H), 7.00–7.20 (m, 3H), 7.25 (dd, 1H), 7.39 (s, 1H), 7.51 (dd, 1H) and 13.0 (br s, 1H). Anal. Calcd for C19H20N2O3: C, 70.35; H, 6.21; N, 8.64. Found: C, 70.33; H, 6.18; N, 8.60.

Workup

  1. customThe solvents were removed
  2. customthe residual oil was chromatographed on silica gel
  3. customto give, as the first product
  4. washeluted from the column, 2.5 g of product, which
  5. customwas crystallized from ether

Sources & evidence

ORD record
ord-43643c00c98749199b9b8df0fab89132
Source dataset
uspto-grants-2006_09
Patent number
US07112603B2

Reaction notes

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