1,2-Dichloroethane → HCID 178509905, 화합물

HRID 1875086노트

반응식

HRID 1875086 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.[Cl:35][C:36]1[N:37]=[C:38]([CH2:52][O:53][Si](C(C)(C)C)(C)C)[N:39](COCC[Si](C)(C)C)[C:40]=1[C:41](O)=[O:42].C(=O)(O)[O-].[Na+].FC(F)(F)C(O)=O>CN(C=O)C>[Br:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][NH:15][C:41]([C:40]2[NH:39][C:38]([CH2:52][OH:53])=[N:37][C:36]=2[Cl:35])=[O:42])=[C:18]([F:34])[C:19]=1[O:24][C:25]1[CH:26]=[C:27]([C:28]#[N:29])[CH:30]=[C:31]([Cl:33])[CH:32]=1

참가 물질

8

반응물 6

HCID 111,2-DichloroethaneHCID 6422Trifluoroacetic acidHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 671971663-{[3-(Aminomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrileHCID 684865744-chloro-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxylic acid

생성물 1

HCID 178509905HCID 178509905, 화합물수율 49%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

EDC (0.025 g, 0.131 mmol) and HOBT (0.018 g, 0.131 mmol) were added to a solution of 3-{[3-(aminomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.042 g, 0.119 mmol) and 4-chloro-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxylic acid (0.050 g, 0.119 mmol) in DMF (2 mL). The mixture was stirred at RT for 4 hrs, saturated sodium bicarbonate was added and the solution was extracted with EtOAc. The organic layer was dried over sodium sulfate and concentrated. The crude product was dissolved in dichloromethane (2 mL) and trifluoroacetic acid (0.3 mL, 3.89 mmol) was added. 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 (0.030 g, 47%) as a white powder. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.99 (br. s., 1H), 8.32-8.41 (m, 1H), 7.79-7.84 (m, 1H), 7.57-7.65 (m, 1H), 7.47-7.52 (m, 1H), 7.44 (t, 1H), 7.31 (t, 1H), 5.54 (br. s., 1H), 4.45-4.53 (m, 2H), 4.37-4.44 (m, 2H). ES MS: m/z 512, 514.

후처리

  1. extractionthe solution was extracted with EtOAc
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. dissolutionThe crude product was dissolved in dichloromethane (2 mL)
  5. stirringThe mixture was stirred at RT overnight
  6. customThe solvent was evaporated
  7. customthe residue was purified by reverse phase HPLC (acetonitrile:water with 0.1% formic acid)

출처 및 근거

ORD 기록
ord-3b5861b3961f4c879344600e9ebcd63a
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

반응 노트

불러오는 중…