Cyclopropanemethanol → HCID 178524993, compound

HRID 402648Notes

Reaction equation

HRID 402648 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]([F:23])=[CH:19][CH:18]=3)=[C:13]([C:24]([O:26][CH3:27])=[O:25])[C:12]2=[O:28])=[CH:2]1.[CH:29]1(CO)[CH2:31][CH2:30]1>CN(C)C(=O)C.[Zn]>[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:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)=[C:13]([C:24]([O:26][CH2:27][CH:29]3[CH2:31][CH2:30]3)=[O:25])[C:12]2=[O:28])=[CH:2]1

Participants

5

Reactant 2

HCID 75644CyclopropanemethanolHCID 178498741HCID 178498741, compound

Product 1

HCID 178524993HCID 178524993, compoundYield 19.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 31374DimethylacetamideSolvent

Procedure

Under a nitrogen atmosphere, a solution of the compound (0.038 g, 0.10 mmol) of Example 51, cyclopropyl carbinol (0.10 mL, 1.3 mmol) and zinc cluster catalyst (Zn4(OCOCF3)6O) (0.0019 g, 0.0020 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 (0.0080 g, y. 19%).

Workup

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

Sources & evidence

ORD record
ord-e2318f0142c742ce806e81b9ee056503
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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