Diisopropylethylamine → (R)-2-(6-(2-chloropyridin-4-yloxy)benzo[d]thiazol-2-ylamino)-4-methylpentan-1-ol

HRID 2370531

반응식

HRID 2370531 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:20]=[CH:19][C:12]3[N:13]=[C:14](S(C)=O)[S:15][C:11]=3[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[NH2:21][C@H:22]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:23][OH:24].CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:20]=[CH:19][C:12]3[N:13]=[C:14]([NH:21][C@H:22]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:23][OH:24])[S:15][C:11]=3[CH:10]=2)[CH:5]=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 2724002D(-)-LeucinolHCID 577254306-(2-Chloropyridin-4-yloxy)-2-(methylsulfinyl)benzo[d]thiazole

생성물 1

HCID 57725426(R)-2-(6-(2-chloropyridin-4-yloxy)benzo[d]thiazol-2-ylamino)-4-methylpentan-1-ol수율 38.8%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
100 °C

실험 절차

To the solution of 6-(2-chloropyridin-4-yloxy)-2-(methylsulfinyl)benzo[d]thiazole (26 mg, 80 μmol) in 400 μL of NMP was added (R)-2-amino-4-methylpentan-1-ol (33 μL, 250 μmol) and DIPEA (17 μL, 100 μmol). The reaction solution was stirred at 100° C. for 18 hours. The crude reaction solution was purified on prep HPLC and evaporated in vaccuo to give (R)-2-(6-(2-chloropyridin-4-yloxy)benzo[d]thiazol-2-ylamino)-4-methylpentan-1-ol (12 mg, 31 μmol) as powder. ES/MS m/z 378.1 (MH+).

후처리

  1. customThe crude reaction solution
  2. customwas purified on prep HPLC
  3. customevaporated in vaccuo

출처 및 근거

ORD 기록
ord-75b7c0ae9c69476da4412313c52ac0a9
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08710048B2

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