(4-Amino-3-methoxy-benzyl)-benzyl-carbamic acid tert-butyl ester → Benzyl-{4-[3-(5-cyano-pyrazin-2-yl)-ureido]-3-methoxy-benzyl}-carbamic acid tert-butyl ester

HRID 1019754노트

반응식

HRID 1019754 반응식
[C:1]([O:5][C:6](=[O:25])[N:7]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([O:23][CH3:24])[CH:17]=1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[C:26]([C:28]1[N:29]=[CH:30][C:31]([NH:34][C:35](=O)[O:36]C2C=CC=CC=2)=[N:32][CH:33]=1)#[N:27]>CN(C=O)C>[C:1]([O:5][C:6](=[O:25])[N:7]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:35]([NH:34][C:31]2[CH:30]=[N:29][C:28]([C:26]#[N:27])=[CH:33][N:32]=2)=[O:36])=[C:18]([O:23][CH3:24])[CH:17]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 21034184(4-Amino-3-methoxy-benzyl)-benzyl-carbamic acid tert-butyl esterHCID 22064357Phenyl 5-cyanopyrazin-2-ylcarbamate

생성물 1

HCID 67469180Benzyl-{4-[3-(5-cyano-pyrazin-2-yl)-ureido]-3-methoxy-benzyl}-carbamic acid tert-butyl ester수율 67.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

(4-Amino-3-methoxy-benzyl)-benzyl-carbamic acid tert-butyl ester (0.25 g, 0.73 mmol) and phenyl 5-cyanopyrazin-2-ylcarbamate (0.21 g 0.87 mmol) (Example 10) were dissolved in DMF (2.5 mL) and heated at 80° C. for 2 hours. The mixture was allowed to cool to room temperature then partitioned between water (15 mL) and EtOAc (25 mL). The separated aqueous layer was extracted with EtOAC (25 ml), and then the combined organic extracts were washed with water (15 mL), brine (10 mL), dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by column chromatography on neutral silica gel using 15-25% EtOAc in hexane to afford the title compound (0.24 g, 67%).

후처리

  1. temperatureto cool to room temperature
  2. customthen partitioned between water (15 mL) and EtOAc (25 mL)
  3. extractionThe separated aqueous layer was extracted with EtOAC (25 ml)
  4. washthe combined organic extracts were washed with water (15 mL), brine (10 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on neutral silica gel using 15-25% EtOAc in hexane

출처 및 근거

ORD 기록
ord-f15812e27e2e479c84682c7fa7e02bc8
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716287B2

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