Hydrochloric Acid → Methyl 6-cyano-7-(4-(8-methoxyquinolin-3-ylcarbamoyl)phenoxy)chroman-4-carboxylate

HRID 1626395노트

반응식

HRID 1626395 반응식
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:23]([O:25][CH3:26])=[O:24])#[N:2].[CH3:27][O:28][C:29]1[CH:30]=[CH:31][CH:32]=[C:33]2[C:38]=1[N:37]=[CH:36][C:35]([NH2:39])=[CH:34]2.C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.O>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:14]1[CH:15]=[CH:16][C:17]([C:18](=[O:19])[NH:39][C:35]3[CH:36]=[N:37][C:38]4[C:33]([CH:34]=3)=[CH:32][CH:31]=[CH:30][C:29]=4[O:28][CH3:27])=[CH:21][CH:22]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:23]([O:25][CH3:26])=[O:24])#[N:2]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 189450658-Methoxyquinolin-3-amineHCID 462211084-(6-Cyano-4-(methoxycarbonyl)-chroman-7-yloxy)benzoic acid

생성물 1

HCID 67289723Methyl 6-cyano-7-(4-(8-methoxyquinolin-3-ylcarbamoyl)phenoxy)chroman-4-carboxylate수율 42%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

Dissolved 4-(6-cyano-4-(methoxycarbonyl)chroman-7-yloxy)benzoic acid (0.10 g, 0.29 mmol), 8-methoxyquinolin-3-amine (0.050 g, 0.29 mmol), and HOAT (0.039 g, 0.29 mmol) in dry DMF (1 mL) at ambient temperature. EDCI (0.049 g, 0.32 mmol) was added and the mixture stirred at ambient temperature overnight. The reaction was diluted with excess water, acidified with 10% HCl and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated. The crude material was purified by silica gel column chromatography eluting with 2-5% methanol/dichloromethane to provide the desired product (0.061 g, 42%) as a colorless foam.

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by silica gel column chromatography
  6. washeluting with 2-5% methanol/dichloromethane

출처 및 근거

ORD 기록
ord-3f4a4b17c6094a8392b5ebd647886d50
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785445B2

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