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Diisopropylethylamine → HCID 59451573, 화합물

HRID 1875030
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HRID 1875030 반응식
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:25][CH2:26][C:27]1[C:28]([F:44])=[C:29]([O:34][C:35]2[CH:36]=[C:37]([CH:40]=[C:41]([Cl:43])[CH:42]=2)[C:38]#[N:39])[C:30]([Cl:33])=[CH:31][CH:32]=1.CC(OC([N:52]1[C:60]2[C:55](=[CH:56][CH:57]=[C:58]([NH:61][C:62](=[O:70])[CH2:63][CH2:64][O:65][C:66]([CH3:69])([CH3:68])[CH3:67])[CH:59]=2)[CH:54]=[C:53]1[C:71](O)=[O:72])=O)(C)C.C(N(C(C)C)CC)(C)C>CN(C=O)C>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][NH:25][C:71]([C:53]2[NH:52][C:60]3[C:55]([CH:54]=2)=[CH:56][CH:57]=[C:58]([NH:61][C:62](=[O:70])[CH2:63][CH2:64][O:65][C:66]([CH3:68])([CH3:67])[CH3:69])[CH:59]=3)=[O:72])=[C:28]([F:44])[C:29]=1[O:34][C:35]1[CH:36]=[C:37]([C:38]#[N:39])[CH:40]=[C:41]([Cl:43])[CH:42]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 594513923-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrileHCID 68485877HCID 68485877, 화합물

생성물 1

HCID 59451573HCID 59451573, 화합물수율 58.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

HATU (0.090 g, 0.237 mmol) was added to a solution of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.0491 g, 0.158 mmol), 1-{[(1,1-dimethylethyl)oxy]carbonyl}-6-({3-[(1,1-dimethylethyl)oxy]propanoyl}amino)-1H-indole-2-carboxylic acid (0.048 g, 0.158 mmol) and diisopropylethylamine (0.041 mL, 0.237 mmol) in DMF (1 mL). The mixture was stirred at room temperature overnight. The reaction mixture was extracted with ethyl acetate and water. The organic layer was washed with water, dried over sodium sulfate and concentrated. The residue was purified by flash chromatography (hexane:ethyl acetate) to give the title compound (0.055 g, 58%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.47 (s, 1H), 9.81 (s, 1H), 8.89 (t, 1H), 7.94 (s, 1H), 7.78 (s, 1H), 7.39-7.53 (m, 4H), 7.36 (t, 1H), 7.03-7.12 (m, 2H), 4.52 (d, 2H), 3.57 (t, 2H), 2.36-2.49 (m, 2H), 1.10 (s, 9H). ES MS: m/z 597 (M+1).

후처리

  1. extractionThe reaction mixture was extracted with ethyl acetate and water
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (hexane:ethyl acetate)

출처 및 근거

ORD 기록
ord-00994645870a4a5da7a6e7ed5de09e93
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08304419B2

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