Potassium Carbonate → N'-(5-{[(2R)-1-(2-tert-butoxyethyl)pyrrolidin-2-yl]methoxy}-2-cyano-4-methoxyphenyl)-N,N-dimethylimidoformamide

HRID 749175Notes

Reaction equation

HRID 749175 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH2:12][C@H:13]2[CH2:17][CH2:16][CH2:15][NH:14]2)=[CH:5][C:4]=1[N:18]=[CH:19][N:20]([CH3:22])[CH3:21])#[N:2].Br[CH2:24][CH2:25][O:26][C:27]([CH3:30])([CH3:29])[CH3:28].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:27]([O:26][CH2:25][CH2:24][N:14]1[CH2:15][CH2:16][CH2:17][C@@H:13]1[CH2:12][O:11][C:6]1[C:7]([O:9][CH3:10])=[CH:8][C:3]([C:1]#[N:2])=[C:4]([N:18]=[CH:19][N:20]([CH3:21])[CH3:22])[CH:5]=1)([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123592832-(2-Bromoethoxy)-2-methylpropaneHCID 68988386HCID 68988386, compound

Product 1

HCID 68989803N'-(5-{[(2R)-1-(2-tert-butoxyethyl)pyrrolidin-2-yl]methoxy}-2-cyano-4-methoxyphenyl)-N,N-dimethylimidoformamideYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N′-(2-cyano-4-methoxy-5-[(2R)-pyrrolidin-2-ylmethoxy]phenyl)-N,N-dimethylimidoformamide (1.23 g, 4.06 mmol) in dimethylformamide (13 ml) was reacted with 2-(2-bromoethoxy)-2-methylpropane (809 mg, 4.47 mmol) in the presence of potassium carbonate (842 mg, 6.1 mmol) at 50° C. for 5 hours. The solvent was then evaporated, and the residue purified by chromatography on silica gel, eluting with dichloromethane:methanol (98:2) then (95:5), to yield N′-(5-{[(2R)-1-(2-tert-butoxyethyl)pyrrolidin-2-yl]methoxy}-2-cyano-4-methoxyphenyl)-N,N-dimethylimidoformamide (908 mg, 56% yield):

Workup

  1. customThe solvent was then evaporated
  2. customthe residue purified by chromatography on silica gel
  3. washeluting with dichloromethane:methanol (98:2)

Sources & evidence

ORD record
ord-4274dd09c8724b418274e3aa0ea3203f
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

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