Sodium Hydroxide → 4-[1-Ethyl-7-(2-piperidin-4-yl-ethyl)1H-imidazo[4,5-c]pyridin-2-yl]-furazan-3-ylamine

HRID 1394222Notes

Reaction equation

HRID 1394222 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=[CH2:15])[CH2:10][CH2:9]1)=O)(C)(C)C.C12BC(CCC1)CCC2.Br[C:26]1[C:27]2[N:34]([CH2:35][CH3:36])[C:33]([C:37]3[C:38]([NH2:42])=[N:39][O:40][N:41]=3)=[N:32][C:28]=2[CH:29]=[N:30][CH:31]=1.[OH-].[Na+]>O1CCCC1.ClCCl>[CH2:35]([N:34]1[C:27]2[C:26]([CH2:15][CH2:14][CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[CH:31][N:30]=[CH:29][C:28]=2[N:32]=[C:33]1[C:37]1[C:38]([NH2:42])=[N:39][O:40][N:41]=1)[CH3:36]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 10910832tert-Butyl 4-ethenylpiperidine-1-carboxylateHCID 443971924-(7-Bromo-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)-1,2,5-oxadiazol-3-amine

Product 1

HCID 596817624-[1-Ethyl-7-(2-piperidin-4-yl-ethyl)1H-imidazo[4,5-c]pyridin-2-yl]-furazan-3-ylamineYield 6.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-vinyl-piperidine-1-carboxylic acid tert-butyl ester (WO 9620192) (1.2 mM: 252 mg) in dry tetrahydrofuran (4 ml) was treated with a 0.5M solution of 9-borabicyclo[3.3.1]-nonane in tetrahydrofuran (1.2 mM; 2.4 ml) and stirred at room temperature for 6 hours under argon. The mixture was treated with the product of Example 100 (1.0 mM; 309 mg), 1,1′-bis(diphenylphosphino)ferrocene dichloro palladium(II) complex with dichloromethane (25 mg) and a 3M aqueous solution of sodium hydroxide (1 ml). The resulting mixture was heated at reflux under argon for 18 hours and purified on a 5 g SCX ion exchange cartridge. After removal of the solvent in vacuo the resulting yellow gum was treated with trifluoroacetic acid at room temperature for 2 hours and the solution passed through a 5 g SCX ion exchange cartridge. The solvent was removed in vacuo and the residue purified on a 5 g silica solid phase extraction cartridge eluting with 1-5-94 ammonia-methanol-dichloromethane to give the title compound as a white solid (23 mg). MS (ES+) m/e 342 [M+H]+.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux under argon for 18 hours
  3. custompurified on a 5 g SCX ion exchange cartridge
  4. customAfter removal of the solvent in vacuo the resulting yellow gum
  5. additionwas treated with trifluoroacetic acid at room temperature for 2 hours
  6. customThe solvent was removed in vacuo
  7. customthe residue purified on a 5 g silica solid phase extraction cartridge
  8. washeluting with 1-5-94 ammonia-methanol-dichloromethane

Sources & evidence

ORD record
ord-1c5ea4a17e93404c85d8520617f5ce7b
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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