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

HRID 1394219노트

반응식

HRID 1394219 반응식
[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]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 10448961Tert-butyl 4-(iodomethyl)piperidine-1-carboxylate2회HCID 596818031H-Imidazo[4,5-c]pyridin-7-ol, 2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-bbb50fbdeb5646f99c3f038aa7724980
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07348339B2

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