Cyclopropanemethanol → HCID 178429075, compound

HRID 402686Notes

Reaction equation

HRID 402686 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]CC)=[O:31])[C:12]2=[O:35])=[CH:2]1.[CH:36]1([CH2:39][OH:40])[CH2:38][CH2:37]1>CN(C)C(=O)C.[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:40][CH2:39][CH:36]3[CH2:38][CH2:37]3)=[O:31])[C:12]2=[O:35])=[CH:2]1

Participants

5

Reactant 2

HCID 75644CyclopropanemethanolHCID 178469594HCID 178469594, compound

Product 1

HCID 178429075HCID 178429075, compoundYield 15.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

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, cyclopropyl carbinol (0.10 mL, 1.3 mmol) and zinc cluster catalyst (Zn4(OCOCF3)6O) (0.0033 g, 0.0035 mmol) in N,N-dimethylacetamide (0.9 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 (0.0029 g, y. 8%).

Workup

  1. temperatureCooled to ambient temperature
  2. customthe precipitate was removed by filtration
  3. customThe filtrate was purified by preparative HPLC

Sources & evidence

ORD record
ord-e9d9080ac52c4577a7b5787eefd3ae8f
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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