Dimethylacetamide → HCID 178450766, compound

HRID 402688Notes

Reaction equation

HRID 402688 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]2[O:15][C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]([CH3:28])[CH3:27])=[CH:19][C:18]=3[CH3:29])=[C:13]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:12]2=[O:35])=[CH:2]1.CN(C)[C:38](=O)[CH3:39]>C(O)CCC.[Zn]>[CH:30]([OH:32])=[O:31].[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]2[O:15][C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]([CH3:28])[CH3:27])=[CH:19][C:18]=3[CH3:29])=[C:13]([C:30]([O:32][CH2:33][CH2:34][CH2:38][CH3:39])=[O:31])[C:12]2=[O:35])=[CH:2]1

Participants

5

Reactant 2

HCID 31374DimethylacetamideHCID 178469594HCID 178469594, compound

Product 1

HCID 178450766HCID 178450766, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 2631-ButanolSolvent

Procedure

A solution of ethyl 5-[(1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-2-({4-[2-(dimethylamino)ethoxy]-2-methylphenyl}amino)-4-oxo-4,5-dihydrofuran-3-carboxylate (0.033 g, 0.070 mmol) which similarly prepared according to the procedure described in the Example 111, and zinc cluster catalyst (Zn4(OCOCF3)6O) (0.0033 g, 0.0035 mmol) in n-butanol (0.5 mL) and N,N-dimethylacetamide (0.5 mL) was stirred with the microwave synthesizer (Biotage Initiator™) at 150° C. for 30 min. Cooled to ambient temperature, the precipitate was removed by filtration. The filtrate was purified by preparative HPLC to afford the titled compound as solid (0.011 g, y. 31%).

Workup

  1. customthe precipitate was removed by filtration
  2. customThe filtrate was purified by preparative HPLC

Sources & evidence

ORD record
ord-202d1b03ed304c6e807231df7d18f237
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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