7-(2-{1-[2-(4-Cyanophenoxy)ethyl]-3,3-dimethylureido}ethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester → 1-[2-(4-Cyanophenoxy)ethyl]-3,3-dimethyl-1-[2-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethyl]urea

HRID 899130Notes

Reaction equation

HRID 899130 reaction equation
C(OC([N:8]1[CH2:15][CH:14]2[O:16][CH:10]([CH2:11][N:12]([CH2:17][CH2:18][N:19]([CH2:25][CH2:26][O:27][C:28]3[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=3)[C:20]([N:22]([CH3:24])[CH3:23])=[O:21])[CH2:13]2)[CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[C:34]([C:31]1[CH:30]=[CH:29][C:28]([O:27][CH2:26][CH2:25][N:19]([CH2:18][CH2:17][N:12]2[CH2:11][CH:10]3[O:16][CH:14]([CH2:15][NH:8][CH2:9]3)[CH2:13]2)[C:20]([N:22]([CH3:24])[CH3:23])=[O:21])=[CH:33][CH:32]=1)#[N:35]

Participants

4

Reactant 1

HCID 690786487-(2-{1-[2-(4-Cyanophenoxy)ethyl]-3,3-dimethylureido}ethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester

Product 1

HCID 690769821-[2-(4-Cyanophenoxy)ethyl]-3,3-dimethyl-1-[2-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethyl]ureaYield 25.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

7-(2-{1-[2-(4-Cyanophenoxy)ethyl]-3,3-dimethylureido}ethyl)-9-oxa-3,7-di-azabicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester (6.5 g; see Example 5 below) was taken in HCl in dioxane (50 mL) and stirred for 30 min. The reaction mixture was decanted and the solid was taken in a biphasic mixture of dichloromethane and aqueous NaHCO3. The organic layer was separated, washed with water, dried over sodium sulfate and concentrated. Purification by column chromatography yielded 1.3 g of the title compound as pale yellow solid.

Workup

  1. customThe reaction mixture was decanted
  2. additionthe solid was taken in a biphasic mixture of dichloromethane and aqueous NaHCO3
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-9a2b525acd2f400faf5a1c2152fe9405
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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