2-Morpholinoethanol → HCID 178525587, compound

HRID 402637Notes

Reaction equation

HRID 402637 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]C)=[O:25])[C:12]2=[O:28])=[CH:2]1.[OH:29][CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>CN(C)C(=O)C.[Zn]>[CH:24]([OH:26])=[O:25].[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:29][CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[O:25])[C:12]2=[O:28])=[CH:2]1

Participants

5

Reactant 2

HCID 611632-MorpholinoethanolHCID 178498741HCID 178498741, compound

Product 1

HCID 178525587HCID 178525587, compoundYield 28.6%

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, N-(2-hydroxyethyl)morpholine (0.20 mL, 1.6 mmol) and zinc cluster catalyst (Zn4(OCOCF3)6O) (0.0019 g, 0.0020 mmol) in N,N-dimethylacetamide (0.8 mL) was stirred with the microwave synthesizer (Biotage Initiator™) at 150° C. for 40 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 (0.0075 g, y. 15%).

Workup

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

Sources & evidence

ORD record
ord-daf045cde9b240eb90a529f43d87b82b
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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