3-Pyridinecarboxaldehyde → N-[2-(4-Cyanophenoxy)ethyl]-N-{2-[7-(pyridin-3-ylmethyl)-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl]ethyl}methanesulfonamide

HRID 899150Notes

Reaction equation

HRID 899150 reaction equation
[C:1]([C:3]1[CH:27]=[CH:26][C:6]([O:7][CH2:8][CH2:9][N:10]([CH2:15][CH2:16][N:17]2[CH2:24][CH:23]3[O:25][CH:19]([CH2:20][NH:21][CH2:22]3)[CH2:18]2)[S:11]([CH3:14])(=[O:13])=[O:12])=[CH:5][CH:4]=1)#[N:2].[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH:34]=O)[CH:29]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH2:9][N:10]([CH2:15][CH2:16][N:17]2[CH2:24][CH:23]3[O:25][CH:19]([CH2:20][N:21]([CH2:34][C:30]4[CH:29]=[N:28][CH:33]=[CH:32][CH:31]=4)[CH2:22]3)[CH2:18]2)[S:11]([CH3:14])(=[O:13])=[O:12])=[CH:26][CH:27]=1)#[N:2]

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69072689N-[2-(4-Cyanophenoxy)ethyl]-N-[2-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethyl]methanesulfonamide

Product 1

HCID 11698760N-[2-(4-Cyanophenoxy)ethyl]-N-{2-[7-(pyridin-3-ylmethyl)-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl]ethyl}methanesulfonamideYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[2-(4-Cyanophenoxy)ethyl]-N-[2-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethyl]methanesulfonamide (79 mg, 0.2 mmol; see Example 3(ii) above) and pyridine-3-carbaldehyde (36 mg, 0.34 mmol) were dissolved in DCM (4 mL) and shaken for 1.5 h. Sodium triacetoxyborohydride (144 mg, 0.68 mmol) was added and the mixture was shaken overnight. The reaction was quenched with 1 M K2CO3 (2 mL) and was then phase-separated. The aqueous layer was washed with DCM (3×3 mL) and the organic layers were combined and evaporated. The residue was purified by chromatography on silica, which gave 66 mg (68%) of the title compound.

Workup

  1. stirringthe mixture was shaken overnight
  2. customThe reaction was quenched with 1 M K2CO3 (2 mL)
  3. customwas then phase-separated
  4. washThe aqueous layer was washed with DCM (3×3 mL)
  5. customevaporated
  6. customThe residue was purified by chromatography on silica, which

Sources & evidence

ORD record
ord-96d25e9b0a0b46419953d8e0aaf46007
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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