Diisopropylethylamine → AZ-960

HRID 75908

반응식

HRID 75908 반응식
Cl[C:2]1[CH:3]=[C:4](N)[C:5]([NH:17][C@H:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH3:19])=[N:6][C:7]=1[NH:8][C:9]1[CH:13]=[C:12]([CH:14]2CC2)[NH:11][N:10]=1.CC[N:30]([CH:34](C)C)C(C)C.[F:37]C1C=CC([C@@H](N)C)=CC=1>CCCCO.O>[F:37][C:2]1[C:7]([NH:8][C:9]2[CH:13]=[C:12]([CH3:14])[NH:11][N:10]=2)=[N:6][C:5]([NH:17][C@H:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH3:19])=[C:4]([CH:3]=1)[C:34]#[N:30]

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 2779063(S)-1-(4-Fluorophenyl)-ethylamineHCID 68522447(S)-5-Chloro-N6-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(4-fluorophenyl)ethyl)pyridine-2,3,6-triamine

생성물 1

HCID 25099184AZ-960수율 91%

시약·촉매·용매 2

HCID 2631-Butanol용매HCID 962Water용매

반응 조건

온도
130 °C

실험 절차

A suspension of 2,5-difluoro-6-(5-methyl-1H-pyrazol-3-ylamino)nicotinonitrile (Method 41, 0.20 g, 0.85 mmol), DIEA (0.14 g, 1.1 mmol), and (S)-1-(4-fluorophenyl)ethanamine (0.23 g, 1.7 mmol) in n-BuOH (2 ml) was heated to 130° C. for 18 hours. The reaction was then cooled to room temperature, diluted with water (20 ml), and extracted with DCM (2×50 ml). The combined organic fractions were dried over Na2SO4, filtered, and then concentrated. The resulting oil was purified by column chromatography (DCM-MeOH=100:1) to give the title compound (0.27 g, 91%). 1H NMR (400 MHz, CD3OD) δ 7.38-7.32 (m, 3H), 7.03-6.99 (m, 2H), 5.99 (br s, 1H), 5.15-5.14 (m, 1H), 2.24 (s, 3H), 1.53 (d, J=6.8 Hz, 3H). MS: Calcd.: 354. Found: [M+H]+ 355.

후처리

  1. temperatureThe reaction was then cooled to room temperature
  2. extractionextracted with DCM (2×50 ml)
  3. dry with materialThe combined organic fractions were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting oil was purified by column chromatography (DCM-MeOH=100:1)

출처 및 근거

ORD 기록
ord-b8c9e5db3a2648b28c3e65b067b4bb83
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835465B2

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