2-Cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamine → 5-Cyclopropyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid [2-cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide

HRID 1480128

반응식

HRID 1480128 반응식
[CH:1]1([C:4]2[C:5]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])=[CH:6][C:7]([C:10]([OH:12])=O)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.[CH:19]1([CH2:22][C:23]([NH2:31])([CH3:30])[C:24]2[N:28]=[C:27]([CH3:29])[O:26][N:25]=2)[CH2:21][CH2:20]1>>[CH:19]1([CH2:22][C:23]([NH:31][C:10]([C:7]2[CH:6]=[C:5]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])[C:4]([CH:1]3[CH2:2][CH2:3]3)=[CH:9][N:8]=2)=[O:12])([CH3:30])[C:24]2[N:28]=[C:27]([CH3:29])[O:26][N:25]=2)[CH2:21][CH2:20]1

참가 물질

3

반응물 2

HCID 710877912-Cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamineHCID 902036745-Cyclopropyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid

생성물 1

HCID 902149155-Cyclopropyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid [2-cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide

실험 절차

The title compound was synthesized in analogy to Example 63b, using 5-Cyclopropyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid (Example 48c) and 2-Cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamine (Example 66e) as starting materials and the racemate was isolated (43 mg, 32%) as a colorless oil. The racemate was separated into its enantiomers by preparative chiral HPLC (Chiralpak AD, isopropanol/heptane) and the title compound was the first enantiomer collected and isolated as a colorless oil; MS (ESI, m/z): 425.5 (M+H+). The collected enantiomer shows levorotation properties according to the observed optical activity measured during preparative chiral HPLC.

후처리

  1. customthe racemate was isolated (43 mg, 32%) as a colorless oil
  2. customThe racemate was separated into its enantiomers by preparative chiral HPLC (Chiralpak AD, isopropanol/heptane)
  3. customcollected
  4. customisolated as a colorless oil

출처 및 근거

ORD 기록
ord-ee72d1082c52422a8879e1e1d4e7f2d4
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409866B2

연결된 노트

불러오는 중…