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

HRID 899148Notes

Reaction equation

HRID 899148 reaction equation
Cl.C(OC([N:9]1[CH2:16][CH:15]2[O:17][CH:11]([CH2:12][N:13]([CH2:18][CH2:19][N:20]([CH2:25][CH2:26][O:27][C:28]3[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=3)[S:21]([CH3:24])(=[O:23])=[O:22])[CH2:14]2)[CH2:10]1)=O)(C)(C)C>O1CCOCC1>[C:34]([C:31]1[CH:30]=[CH:29][C:28]([O:27][CH2:26][CH2:25][N:20]([CH2:19][CH2:18][N:13]2[CH2:14][CH:15]3[O:17][CH:11]([CH2:10][NH:9][CH2:16]3)[CH2:12]2)[S:21]([CH3:24])(=[O:23])=[O:22])=[CH:33][CH:32]=1)#[N:35]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 690747607-(2-{[2-(4-Cyanophenoxy)ethyl]methanesulfonylamino}ethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester

Product 1

HCID 69072689N-[2-(4-Cyanophenoxy)ethyl]-N-[2-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a saturated solution of HCl(g) in dioxane (100 mL) was added 7-(2-{[2-(4-cyanophenoxy)ethyl]methanesulfonylamino}ethyl)-9-oxa-3,7-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester (3.5 g, 0.0070 mol; see step (i) above), after which the reaction was stirred for 1 h. On completion of the reaction (as determined by TLC), dioxane was decanted and product (semi-solid) dissolved in methanol (25 mL). After concentrating the methanol, dry ether (50 mL) was added and the solvent was again concentrated. This was repeated twice and finally the product was dried under high vacuum. Yield: 3.0 g (99%).

Workup

  1. customwas decanted
  2. dissolutionproduct (semi-solid) dissolved in methanol (25 mL)
  3. concentrationAfter concentrating the methanol, dry ether (50 mL)
  4. additionwas added
  5. concentrationthe solvent was again concentrated
  6. customfinally the product was dried under high vacuum

Sources & evidence

ORD record
ord-08cfc95d1dc8430f8693423a8bc4e9b0
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

Loading…