1,2-Dichloroethane → HCID 178436401, 화합물

HRID 1875100노트

반응식

HRID 1875100 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.[Cl:22][C:23]1[N:24]=[C:25]([CH3:31])[NH:26][C:27]=1[C:28](O)=[O:29].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C([O-])(O)=O.[Na+]>CN(C=O)C.C(OCC)(=O)C>[Cl:22][C:23]1[N:24]=[C:25]([CH3:31])[NH:26][C:27]=1[C:28]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH3:10])=[C:5]([O:11][C:12]2[CH:13]=[C:14]([C:15]#[N:16])[CH:17]=[C:18]([Cl:20])[CH:19]=2)[C:4]=1[F:21])=[O:29]

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 68487595HCID 68487595, 화합물HCID 178432882HCID 178432882, 화합물

생성물 1

HCID 178436401HCID 178436401, 화합물수율 47.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 3-{[3-(aminomethyl)-6-ethyl-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.075 g, 0.246 mmol), 4-chloro-2-methyl-1H-imidazole-5-carboxylic acid (0.040 g, 0.246 mmol), EDC (0.047 g, 0.246 mmol) and HOBT (0.038 g, 0.246 mmol) in DMF (4 ml) was stirred at RT under an atmosphere of nitrogen for 1 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. The material was purified by Reverse Phase HPLC (MeCN/water+0.1% TFA). The desired product was washed with saturated NaHCO3 solution and extraced with ethyl acetate. The organic layer was separated, washed with saturated aqueous NaHCO3 solution (50 mL), water (50 mL), dried over MgSO4, filtered and concentrated to give the title compound (0.052 g, 47%) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 11.06 (br. s., 1H), 7.29 (s, 1H), 7.20 (d, 1H), 7.03-7.12 (m, 3H), 6.97 (s, 1H), 4.67 (d, 2H), 2.53 (q, 2H), 2.37 (s, 3H), 1.13 (t, 3H). LCMS m/z 447.05 (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. customThe material was purified by Reverse Phase HPLC (MeCN/water+0.1% TFA)
  7. washThe desired product was washed with saturated NaHCO3 solution
  8. customThe organic layer was separated
  9. washwashed with saturated aqueous NaHCO3 solution (50 mL), water (50 mL)
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f57de6fd58cb480aacb913285629bc01
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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