Diisopropylethylamine → HCID 86730180, 화합물

HRID 1850143노트

반응식

HRID 1850143 반응식
Cl[C:2]1[N:7]=[C:6]([N:8]2[C@@H:12]([CH:13]([CH3:15])[CH3:14])[CH2:11][O:10][C:9]2=[O:16])[CH:5]=[CH:4][N:3]=1.Cl.C[NH:19][CH2:20][C:21]#[CH:22].[CH:23](N(C(C)C)CC)(C)C>CS(C)=O.CCOC(C)=O>[CH:13]([C@H:12]1[CH2:11][O:10][C:9](=[O:16])[N:8]1[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:19][C@@H:20]([CH3:23])[C:21]#[CH:22])[N:7]=1)([CH3:15])[CH3:14]

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 22416630HCID 22416630, 화합물HCID 86730167(S)-3-(2-chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-one

생성물 1

HCID 86730180HCID 86730180, 화합물수율 31%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of compound (S)-3-(2-Chloro-pyrimidin-4-yl)-4-isopropyl-oxazolidin-2-one (1.03 g, 4.3 mmol) in DMSO (12 mL) was added methyl-prop-2-ynylamine HCl salt (450 mg, 4.3 mmol) and diisopropylethylamine (2.2 mL, 12.6 mmol). The reaction was heated to 110 C for 18 hours. The reaction mixture was diluted with EtOAc (50 mL) and washed with water (25 mL) and brine (25 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified on silica gel column chromatography (EtOAc/Heptane 0 to 75%) provided (S)-4-Isopropyl-3-[2-((S)-1-methyl-prop-2-ynylamino)-pyrimidin-4-yl]-oxazolidin-2-one (360 mg) in 31% yield. LC-MS m/z: 275.1 (M−Boc)+; RT.: 1.33 min.

후처리

  1. temperatureThe reaction was heated to 110 C for 18 hours
  2. washwashed with water (25 mL) and brine (25 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified on silica gel column chromatography (EtOAc/Heptane 0 to 75%)

출처 및 근거

ORD 기록
ord-259f04e011174aee9ae63a5f71dad13e
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957068B2

반응 노트

불러오는 중…