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

HRID 1394219
Notes
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Reaction equation

HRID 1394219 reaction equation
[NH2:1][C:2]1[C:3]([C:7]2[N:8]([CH2:17][CH3:18])[C:9]3[C:14]([OH:15])=[CH:13][N:12]=[CH:11][C:10]=3[N:16]=2)=[N:4][O:5][N:6]=1.C([O-])([O-])=O.[K+].[K+].C(OC([N:32]1[CH2:37][CH2:36][CH:35]([CH2:38]I)[CH2:34][CH2:33]1)=O)(C)(C)C.O>CC(C)=O>[CH2:17]([N:8]1[C:9]2[C:14]([O:15][CH2:38][CH:35]3[CH2:36][CH2:37][NH:32][CH2:33][CH2:34]3)=[CH:13][N:12]=[CH:11][C:10]=2[N:16]=[C:7]1[C:3]1[C:2]([NH2:1])=[N:6][O:5][N:4]=1)[CH3:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 10448961Tert-butyl 4-(iodomethyl)piperidine-1-carboxylate2×HCID 596818032-(4-Amino-1,2,5-oxadiazol-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin-7-ol

Product 1

HCID 112563994-[1-Ethyl-7-(piperidin-4-ylmethoxy)-1H-imidazo[4,5-c]pyridin-2-yl]-furazan-3-ylamineYield 39%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of the product from Example 283 (0.1 g, 0.406 mmol) and K2CO3 (0.112 g, 0.812 mmol) in acetone (3 ml) at −78° C. was treated with 4-iodomethylpiperidine-1-carboxylic acid tert-butyl ester (Villalobos, A; et al, J. Med. Chem., 1994, 37(17), 2721) (0.145 g, 0.447 mmol) and heated at reflux for 18 hours. A further portion of 4-iodomethylpiperidine-1-carboxylic acid tert-butyl ester (0.145 g, 0.447 mmol) was then added and the heating continued for a further 6 hours. The reaction was then cooled, poured into water, extracted with dichloromethane, dried with NaSO4 and reduced. The residue was chromatographed on silica gel eluting with ethyl acetate to afford the title compound, (0.071 g, 39%); MS (ES+) m/e 444 [M+H]+.

Workup

  1. temperature, 1994, 37(17), 2721) (0.145 g, 0.447 mmol) and heated
  2. temperatureat reflux for 18 hours
  3. temperatureThe reaction was then cooled
  4. extractionextracted with dichloromethane
  5. dry with materialdried with NaSO4
  6. customThe residue was chromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-bbb50fbdeb5646f99c3f038aa7724980
Source dataset
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07348339B2

Reaction notes

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