Diisopropylethylamine → ((2S,3R)-2-(((5-Chloropyrimidin-2-yl)amino)methyl)-3-methylpiperidin-1-yl)(5-(4-fluorophenyl)-2-methylthiazol-4-yl)methanone

HRID 60962

반응식

HRID 60962 반응식
[NH2:1][CH2:2][C@@H:3]1[C@H:8]([CH3:9])[CH2:7][CH2:6][CH2:5][N:4]1[C:10]([C:12]1[N:13]=[C:14]([CH3:24])[S:15][C:16]=1[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)=[O:11].Cl[C:26]1[N:31]=[CH:30][C:29]([Cl:32])=[CH:28][N:27]=1.CCN(C(C)C)C(C)C>C(O)(C)C>[Cl:32][C:29]1[CH:28]=[N:27][C:26]([NH:1][CH2:2][C@@H:3]2[C@H:8]([CH3:9])[CH2:7][CH2:6][CH2:5][N:4]2[C:10]([C:12]2[N:13]=[C:14]([CH3:24])[S:15][C:16]=2[C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)=[O:11])=[N:31][CH:30]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 5906412,5-DichloropyrimidineHCID 89739171((2S,3R)-2-(Aminomethyl)-3-methylpiperidin-1-yl)(5-(4-fluorophenyl)-2-methylthiazol-4-yl)methanone

생성물 1

HCID 89739388((2S,3R)-2-(((5-Chloropyrimidin-2-yl)amino)methyl)-3-methylpiperidin-1-yl)(5-(4-fluorophenyl)-2-methylthiazol-4-yl)methanone

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
120 °C

실험 절차

A mixture of ((2S,3R)-2-(aminomethyl)-3-methylpiperidin-1-yl)(5-(4-fluorophenyl)-2-methylthiazol-4-yl)methanone (50 mg, 145 μmol), 2,5-dichloropyrimidine (43 mg, 287 μmol), and DIPEA (75 mg, 431 mol) in isopropanol was stirred at 120° C. for 1 h in a microwave reactor. The crude reaction mixture was purified by reverse-phase preparative HPLC to afford the title compound. MS (ESI) 460 (M+H). 1H NMR (500 MHz, CDCl3) δ 8.25-6.85 (m, 7H), 5.55-2.65 (m, 8H), 1.95-0.85 (m, 8H).

후처리

  1. customThe crude reaction mixture
  2. customwas purified by reverse-phase preparative HPLC

출처 및 근거

ORD 기록
ord-76da8931c29f44a3a1a4c28d8922a86b
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440982B2

연결된 노트

불러오는 중…