1,2-Dichloroethane → HCID 178436403, 화합물

HRID 1875103노트

반응식

HRID 1875103 반응식
[NH2:1][CH2:2][C:3]1[C:4]([F:21])=[C:5]([O:11][C:12]2[CH:13]=[C:14]([CH:17]=[C:18]([Cl:20])[CH:19]=2)[C:15]#[N:16])[C:6]([CH2:9][CH3:10])=[CH:7][CH:8]=1.[N:22]([C:25]1[NH:26][C:27]([C:31](O)=[O:32])=[C:28]([Cl:30])[N:29]=1)=[N+]=[N-].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C([O-])(O)=O.[Na+]>CN(C=O)C.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].C(OCC)(=O)C>[NH2:22][C:25]1[NH:26][C:27]([C:31]([NH:1][CH2:2][C:3]2[CH:8]=[CH:7][C:6]([CH2:9][CH3:10])=[C:5]([O:11][C:12]3[CH:13]=[C:14]([C:15]#[N:16])[CH:17]=[C:18]([Cl:20])[CH:19]=3)[C:4]=2[F:21])=[O:32])=[C:28]([Cl:30])[N:29]=1

참가 물질

9

반응물 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 68487595HCID 68487595, 화합물HCID 1785145302-azido-4-chloro-1H-imidazole-5-carboxylic acid

생성물 1

HCID 178436403HCID 178436403, 화합물수율 53.5%

시약·촉매·용매 3

HCID 131709914Lindlars catalyst촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매2회

실험 절차

A solution of 3-{[3-(aminomethyl)-6-ethyl-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.075 g, 0.246 mmol), 2-azido-4-chloro-1H-imidazole-5-carboxylic acid (0.051 g, 0.271 mmol), EDC (0.052 g, 0.271 mmol) and HOBT (0.041 g, 0.271 mmol) in DMF (4 ml) was stirred at RT under an atmosphere of nitrogen for 16 h then ethyl acetate (100 mL) and saturated aqueous NaHCO3 solution (100 mL) were added. The organic layer was separated, washed with saturated aqueous NaHCO3 solution (100 mL), water (100 mL), dried over MgSO4, filtered and concentrated. Ethyl acetate (20 mL) and Lindlar Catalyst (0.026 g, 0.247 mmol) were added and the mixture was stirred at RT under an atmosphere of hydrogen (55 psig) for 19 h. The vessel was carefully vented and the mixture was filtered thru Celite, concentrated purified by Reverse Phase HPLC (MeCN/water+0.1% TFA) to give the title compound (0.059 g, 51%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.93 (s, 1H), 7.77 (t, 1H), 7.70 (t, 1H), 7.39 (s, 1H), 7.33 (t, 1H), 7.18-7.29 (m, 2H), 5.81 (s, 2H), 4.47 (d, 2H), 2.47-2.54 (m, 2H), 1.08 (t, 3H). LCMS m/z 450.1 (M+H).

후처리

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous NaHCO3 solution (100 mL), water (100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. filtrationthe mixture was filtered thru Celite
  7. concentrationconcentrated
  8. custompurified by Reverse Phase HPLC (MeCN/water+0.1% TFA)

출처 및 근거

ORD 기록
ord-8fffd20813c0484385012115ad9f9977
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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