Triethylamine → [(1-Cyano-4-methoxy-8-phenoxy-isoquinoline-3-carbonyl)-amino]-acetic acid methyl ester

HRID 409287노트

반응식

HRID 409287 반응식
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:6]([O:20][CH3:21])=[C:5]([C:22]([OH:24])=O)[N:4]=1)#[N:2].C(N(CC)CC)C.C(OC(Cl)=O)C(C)C.Cl.[CH3:41][O:42][C:43](=[O:46])[CH2:44][NH2:45]>ClCCl>[CH3:41][O:42][C:43](=[O:46])[CH2:44][NH:45][C:22]([C:5]1[N:4]=[C:3]([C:1]#[N:2])[C:12]2[C:7]([C:6]=1[O:20][CH3:21])=[CH:8][CH:9]=[CH:10][C:11]=2[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:24]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 122755Glycine methyl ester hydrochlorideHCID 671101241-Cyano-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid

생성물 1

HCID 24780690[(1-Cyano-4-methoxy-8-phenoxy-isoquinoline-3-carbonyl)-amino]-acetic acid methyl ester수율 58%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a mixture of 1-cyano-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid (483 mg, 1.51 mmol), triethylamine (466 μL, 3.32 mmol), and dichloromethane (12 mL) was added isobutylchloroformate (211 μL, 1.62 mmol) at 0° C. The mixture was stirred at 0° C. for twenty-five minutes before glycine methyl ester hydrochloride (208 mg, 1.66 mmol) was added. The mixture was stirred at 0° C. for twenty-five minutes and at room temperature for 5.5 hours before it was concentrated. The residue was partitioned between ethyl acetate and 1N HCl. The organic layer was washed with saturated sodium bicarbonate, brine, dried over anhydrous sodium sulfate, concentrated in vacuo and the residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes to give the title compound as a yellow solid (343 mg): MS: (+) m/z 391.95 (M+1).

후처리

  1. additionwas added
  2. concentrationwas concentrated
  3. customThe residue was partitioned between ethyl acetate and 1N HCl
  4. washThe organic layer was washed with saturated sodium bicarbonate, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customthe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes

출처 및 근거

ORD 기록
ord-fc54b76892ee40f592171296b5f3ee2a
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759373B2

반응 노트

불러오는 중…