2-(Dimethylamino)ethanol → 5-{[2-(Dimethylamino)ethyl]oxy}-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

HRID 1623772Notes

Reaction equation

CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH:15][C:16]1[CH:17]=[CH:18][C:19]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[C:20]([CH:30]=1)[C:21]([NH:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)=[O:22].[CH3:39][N:40]([CH3:44])[CH2:41][CH2:42]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1>[CH3:39][N:40]([CH3:44])[CH2:41][CH2:42][O:15][C:16]1[CH:17]=[CH:18][C:19]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[C:20]([CH:30]=1)[C:21]([NH:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)=[O:22]

Participants

Conditions

Temperature: 115 °C

Procedure

A solution of DIAD (252 mg, 1.249 mmol) in toluene (1 ml) was added dropwise to a stirred solution of 5-hydroxy-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide (may be prepared as described in Example 29; 160 mg, 0.50 mmol), 2-(dimethylamino)ethanol (49.0 mg, 0.549 mmol) and Ph3P (328 mg, 1.25 mmol) in toluene (4 ml) under nitrogen at 0° C. The reaction mixture was stirred at 115° C. overnight. The mixture was then cooled and concentrated. The residue was added to water and extracted with ethyl acetate (3×60 ml). The organic phase was washed with saturated brine (30 ml), dried over sodium sulphate and evaporated in vacuo to give crude product. The crude product was added to a silica gel column (40 g) and was eluted with a 20:1 mixture of DCM/methanol (2 l) to yield the title compound as a yellow solid. 50 mg.

Workup

temperatureThe mixture was then cooled
concentrationconcentrated
additionThe residue was added to water
extractionextracted with ethyl acetate (3×60 ml)
washThe organic phase was washed with saturated brine (30 ml)
dry with materialdried over sodium sulphate
customevaporated in vacuo
customto give crude product
washwas eluted with a 20:1 mixture of DCM/methanol (2 l)

Sources & evidence

ORD record: ord-7e76e565e2ad4e43899b4caed8a55584
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778939B2

Reaction notes

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