[6-(4-Cyano-phenyl)-pyridin-2-yl]carbamic acid tert-butyl ester → [6-(4-Aminomethyl-phenyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

HRID 881124

반응식

HRID 881124 반응식
[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2]>CCO.N.O.[Ni]>[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:15]=[CH:16][C:17]([CH2:20][NH2:21])=[CH:18][CH:19]=2)[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 1

HCID 67133691[6-(4-Cyano-phenyl)-pyridin-2-yl]carbamic acid tert-butyl ester

생성물 1

HCID 59166138[6-(4-Aminomethyl-phenyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

시약·촉매·용매 3

HCID 935Nickel촉매HCID 702Ethanol용매HCID 12896473Azane;hydrate용매

실험 절차

A suspension of [6-(4-cyano-phenyl)-pyridin-2-yl]carbamic acid tert-butyl ester (7.0 g, 24 mmol), Raney Ni (1.0 g) in EtOH (500 mL) and NH3.H2O (10 mL) was hydrogenated under H2 (50 psi.) at 50° C. for 6 h. The catalyst was filtered off and the filtrate was concentrated to dryness to give [6-(4-aminomethyl-phenyl)-pyridin-2-yl]-carbamic acid tert-butyl ester, which was used directly in next step. 1H NMR (300 MHz, CDCl3) δ 7.83-7.92 (m, 3 H), 7.70 (t, J=7.8 Hz, 1 H), 7.33-7.40 (m, 4 H), 3.92 (br s, 2 H), 1.53 (s, 9 H).

후처리

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated to dryness

출처 및 근거

ORD 기록
ord-1f438b2614be4dc49f7e3e449c0fb9d0
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993600B2

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