Sodium Chloride → N-[4-(3-bromoanilino)-3-cyano-7-methoxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide

HRID 612127노트

반응식

HRID 612127 반응식
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:20][CH3:21])=[C:16]([NH2:19])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:22]#[N:23])[CH:5]=[CH:6][CH:7]=1.C[CH2:25][N:26]([CH:30]([CH3:32])C)[CH:27](C)C.BrC/C=[CH:36]/[C:37](Cl)=[O:38].[Cl-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:20][CH3:21])=[C:16]([NH:19][C:37](=[O:38])[CH:36]=[CH:32][CH2:30][N:26]([CH3:25])[CH3:27])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:22]#[N:23])[CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 5234Sodium ChlorideHCID 81531DiisopropylethylamineHCID 98206456-Amino-4-[(3-bromophenyl)amino]-7-methoxy-quinoline-3-carbonitrileHCID 11263885(E)-4-Bromo-2-butenoyl Chloride

생성물 1

HCID 54314768N-[4-(3-bromoanilino)-3-cyano-7-methoxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide수율 57.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a mixture of 1.9 g (5.1 mmol) of 4-[(3-bromophenyl)amino]-7-methoxy-6-amino-3-quinolinecarbonitrile and 5.3 ml (31 mmol) of Hunig's base in 110 ml of dry THF at 0° C., with stirring, was added a THF solution containing 5.7 g (31 mmol) of 4-bromo crotonyl chloride dropwise. The mixture was stirred for additional 0.5 hour after addition. 100 ml of saturated sodium chloride solution was added to the reaction mixture, then it was extracted with ethyl acetate. The ethyl acetate solution was dried over sodium sulfate and then was added to 40 ml of dimethyl amine solution (2.0 M in THF) at 0° C. dropwise. The solution was stirred an additional 0.5 hour. The mixture was poured into diluted sodium bicarbonate solution. The organic layer was separated and dried over sodium sulfate. Chromatography gave 1.4 g of beige solid: mass spectrum (electrospray, m/e): M+H 480.0 and 481.9.

후처리

  1. stirringThe mixture was stirred for additional 0.5 hour
  2. additionafter addition
  3. extractionit was extracted with ethyl acetate
  4. dry with materialThe ethyl acetate solution was dried over sodium sulfate
  5. additionwas added to 40 ml of dimethyl amine solution (2.0 M in THF) at 0° C. dropwise
  6. stirringThe solution was stirred an additional 0.5 hour
  7. additionThe mixture was poured into diluted sodium bicarbonate solution
  8. customThe organic layer was separated
  9. dry with materialdried over sodium sulfate

출처 및 근거

ORD 기록
ord-df7626bbc75d466faccfcdce322d4df6
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06002008

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