Hydrochloric Acid → N-[2-(4-Cyanophenoxy)ethyl]-N-[2-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethyl]urea

HRID 899126Notes

Reaction equation

HRID 899126 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]([CH2:23][CH2:24][O:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=3)[C:20]([NH2:22])=[O:21])[CH2:13]2)[CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[C:32]([C:29]1[CH:28]=[CH:27][C:26]([O:25][CH2:24][CH2:23][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]([NH2:22])=[O:21])=[CH:31][CH:30]=1)#[N:33]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 690740097-(2-{1-[2-(4-Cyanophenoxy)ethyl]ureido}ethyl)-9-oxa-3,7-diazabicyclo-[3.3.1]nonane-3-carboxylic acid tert-butyl ester

Product 1

HCID 69070172N-[2-(4-Cyanophenoxy)ethyl]-N-[2-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethyl]urea

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

7-(2-{1-[2-(4-Cyanophenoxy)ethyl]ureido}ethyl)-9-oxa-3,7-diazabicyclo-[3.3.1]nonane-3-carboxylic acid tert-butyl ester (6.44 g; see step (i) above) was added to a solution of HCl-saturated, dry dioxane (300 mL) at 0° C. The reaction was then stirred at rt for 1 hr. The resulting precipitate was filtered under N2, washed with dry ether and then dried under vacuum to provide the title compound. Yield: 6 g.

Workup

  1. filtrationThe resulting precipitate was filtered under N2
  2. washwashed with dry ether
  3. customdried under vacuum

Sources & evidence

ORD record
ord-ff415a9aaa8a45c2b88dde06f6042f77
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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