1-Butanol → HCID 178458645, 화합물

HRID 75873

반응식

HRID 75873 반응식
C1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:18]([F:19])=[CH:17][C:13]([C:14]([NH2:16])=O)=[C:12](N[C@H](C4C=CC(F)=CC=4)C)[N:11]=3)[CH:5]=2)CC1.[F:30][C:31]1[CH:36]=[CH:35][C:34]([C@@H:37]([NH2:39])[CH3:38])=[CH:33][CH:32]=1.CCN(C(C)C)[CH:43]([CH3:45])[CH3:44].CCCC[OH:53]>>[F:19][C:18]1[C:10]([NH:9][C:6]2[CH:5]=[C:4]([O:53][CH:43]([CH3:45])[CH3:44])[NH:8][N:7]=2)=[N:11][C:12]([NH:39][C@H:37]([C:34]2[CH:35]=[CH:36][C:31]([F:30])=[CH:32][CH:33]=2)[CH3:38])=[C:13]([CH:17]=1)[C:14]#[N:16]

참가 물질

5

반응물 4

HCID 2631-ButanolHCID 81531DiisopropylethylamineHCID 2779063(S)-1-(4-Fluorophenyl)-ethylamineHCID 67455185(S)-6-(5-Cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoro-2-(1-(4-fluorophenyl)ethylamino)nicotinamide

생성물 1

HCID 178458645HCID 178458645, 화합물수율 48%

반응 조건

온도
135 °C

실험 절차

2-Chloro-5-fluoro-6-(5-isopropoxy-1H-pyrazol-3-ylamino)nicotinonitrile (Method 2; 1.4 g, 5.0 mmol) and (S)-1-(4-fluorophenyl)ethanamine (1.0 g, 9.0 mmol) were added to a solution of n-BuOH (8 ml) and DIEA (0.8 g, 6.0 mmol) in a sealed tube. The reaction was heated to 135° C. for 48 hrs, cooled to 25° C., and concentrated. The resulting residue was purified by column chromatography (DCM-MeOH=80:1) to give the title compound (0.90 g, 48%). 1H NMR (400 MHz, CD3OD) δ 7.43 (d, J=10.5 Hz, 1H), 7.39-7.35 (m, 2H), 7.04-6.99 (m, 2H), 5.47 (s, 1H), 5.12-5.11 (m, 1H), 4.60-4.51 (m, 1H), 1.56 (d, J=7.0 Hz, 3H), 1.33-1.30 (m, 6H). MS: Calcd.: 398. Found: [M+H]+ 399.

후처리

  1. temperaturecooled to 25° C.
  2. concentrationconcentrated
  3. customThe resulting residue was purified by column chromatography (DCM-MeOH=80:1)

출처 및 근거

ORD 기록
ord-7eed2fd2a9744cafbb38b9dc96fedbde
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835465B2

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