1,2-Dichloroethane → HCID 178509909, 화합물

HRID 1875082노트

반응식

HRID 1875082 반응식
C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH2:15][CH2:16][C:17]1[C:18]([F:34])=[C:19]([O:24][C:25]2[CH:26]=[C:27]([CH:30]=[C:31]([Cl:33])[CH:32]=2)[C:28]#[N:29])[C:20]([Br:23])=[CH:21][CH:22]=1.CC(OC([N:42](C(OC(C)(C)C)=O)[C:43]1[NH:44][C:45]([C:49](O)=[O:50])=[C:46]([Cl:48])[N:47]=1)=O)(C)C.[F:59][C:60]([F:65])([F:64])[C:61]([OH:63])=[O:62]>CN(C=O)C.ClCCl>[F:59][C:60]([F:65])([F:64])[C:61]([OH:63])=[O:62].[NH2:42][C:43]1[NH:44][C:45]([C:49]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[C:19]([O:24][C:25]3[CH:26]=[C:27]([C:28]#[N:29])[CH:30]=[C:31]([Cl:33])[CH:32]=3)[C:18]=2[F:34])=[O:50])=[C:46]([Cl:48])[N:47]=1

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 6422Trifluoroacetic acidHCID 757711-HydroxybenzotriazoleHCID 671971663-{[3-(Aminomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrileHCID 178454348HCID 178454348, 화합물

생성물 1

HCID 178509909HCID 178509909, 화합물수율 18%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

EDC (0.029 g, 0.152 mmol) and HOBT (0.021 g, 0.152 mmol) were added to a solution of 3-{[3-(aminomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.049 g, 0.138 mmol) and 2-(bis{[(1,1-dimethylethyl)oxy]carbonyl}amino)-4-chloro-1H-imidazole-5-carboxylic acid (0.050 g, 0.138 mmol) in DMF (2 mL). The mixture was stirred at RT for 1 hr. The reaction mixture was extracted with EtOAc and saturated sodium bicarbonate. The organic layer was dried over sodium sulfate and concentrated to an oil. Dichloromethane (2 mL) and trifluoroacetic acid (0.5 mL, 6.49 mmol) were added and the mixture was stirred at RT overnight. The solvent was evaporated and the residue was purified by reverse phase HPLC (acetonitrile:water with 0.1% formic acid) to give the title compound (0.0103 g, 18%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.05 (br. s., 1H), 7.75-7.85 (m, 2H), 7.61 (d, 1H), 7.49 (s, 1H), 7.43 (m, 1H), 7.21-7.32 (m, 1H), 5.82 (br. s., 2H), 4.47 (d, 2H). LCMS: m/z 499 (M+1).

후처리

  1. extractionThe reaction mixture was extracted with EtOAc and saturated sodium bicarbonate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated to an oil
  4. stirringthe mixture was stirred at RT overnight
  5. customThe solvent was evaporated
  6. customthe residue was purified by reverse phase HPLC (acetonitrile:water with 0.1% formic acid)

출처 및 근거

ORD 기록
ord-8d0452a4307040c1ae1a1d58b0c1340e
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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