p-Toluenesulfonic acid → 3-piperidin-4-yl-3H-imidazo[4,5-c]pyridine

HRID 1434608노트

반응식

HRID 1434608 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][N+:7]([O-])=[CH:6][C:5]=1[NH:11][CH:12]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]1)([O-])=O.[CH:25](OC)(OC)OC.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[NH:15]1[CH2:14][CH2:13][CH:12]([N:11]2[C:5]3[CH:6]=[N:7][CH:8]=[CH:9][C:4]=3[N:1]=[CH:25]2)[CH2:17][CH2:16]1

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 57935996Tert-butyl 4-[(4-nitro-1-oxidopyridin-3-yl)amino]piperidine-1-carboxylate

생성물 1

HCID 579359853-piperidin-4-yl-3H-imidazo[4,5-c]pyridine

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
105 °C

실험 절차

To tert-butyl 4-[(4-nitro-1-oxidopyridin-3-yl)amino]piperidine-1-carboxylate (1.6 g) in toluene (3 ml) was added trimethyl orthoformate (3.6 ml) followed by p-toluenesulfonic acid (105 mg) and the resulting mixture was heated to 105° C. for 4 hours. The mixture was cooled and partitioned between ethyl acetate (75 ml) and water (75 ml). The organic layer was washed with brine, dried and evaporated to dryness to give the title compound as a solid. Yield 1.18 g. NMR (CDCl3) 1.5 (s, 9H), 2.1 (m, 2H), 2.25 (m, 2H), 3.0 (m, 2H), 4.4 (m, 3H), 7.7 (dd, 1H), 8.1 (s, 1H), 8.5 (d, 1H), 8.9 (s, 1H).

후처리

  1. temperatureThe mixture was cooled
  2. custompartitioned between ethyl acetate (75 ml) and water (75 ml)
  3. washThe organic layer was washed with brine
  4. customdried
  5. customevaporated to dryness

출처 및 근거

ORD 기록
ord-7987e2ceba6b47c5aa0208e67b2e34f7
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07615555B2

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