2-(Dimethylamino)ethanol → HCID 86673050, compound

HRID 1853282Notes

Reaction equation

HRID 1853282 reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][OH:24].CCOC(/N=N/C(OCC)=O)=O.[C:38]([O:42][N:43]=[C:44]1[C:53]2[C:48](=[CH:49][CH:50]=[C:51](O)[CH:52]=2)[O:47][C:46]([C:55]2[N:56]=[CH:57][C:58]3[C:63]([CH:64]=2)=[CH:62][CH:61]=[CH:60][CH:59]=3)=[CH:45]1)([CH3:41])([CH3:40])[CH3:39].[Na]>O1CCCC1>[C:38]([O:42][N:43]=[C:44]1[C:53]2[C:48](=[CH:49][CH:50]=[C:51]([CH2:20][N:21]3[CH2:25][CH2:1][O:24][CH2:23][CH2:22]3)[CH:52]=2)[O:47][C:46]([C:55]2[N:56]=[CH:57][C:58]3[C:63]([CH:64]=2)=[CH:62][CH:61]=[CH:60][CH:59]=3)=[CH:45]1)([CH3:41])([CH3:40])[CH3:39]

Participants

7

Reactant 5

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 5360545SodiumHCID 5462977Diethyl azodicarboxylateHCID 86673049HCID 86673049, compound

Product 1

HCID 86673050HCID 86673050, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold solution of triphenylphosphine (110 mg, 0.41 mmol) in tetrahydrofuran (3 ml) under argon were successively added 2-dimethylamino-ethanol (30 μl, 0.27 mmol), a solution of diethylazodicarboxylate (40% in toluene, 190 μl, 0.41 mmol) and 6-hydroxy-2-isoquinolin-3-yl-chromen-4-one O-tert-butyl oxime (100 mg, 0.27 mmol). The solution was stirred at room temperature for 18 hours. The mixture was poured onto a saturated solution of sodium hydrogenocarbonate and extracted three times with dichloromethane. The organic layers were washed with brine, dried over sodium sulfate and concentrated to dryness to yield 2-isoquinolin-3-yl-6-(morpholin-4-yl-methyl)-chromen-4-one O-tert-butyl oxime (30 mg, 22%) as a yellow solid after purification by flash chromatography over silica gel (dichloromethane/methanol: 0-20%)

Workup

  1. extractionextracted three times with dichloromethane
  2. washThe organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2777885a72e14cc89e482d8cfe444ab2
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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