3-Chloro-4-fluoroaniline → 5-[4-(3-chloro-4-fluoro-phenylamino)-2-oxo-1,2-dihydro-pyrrolo [2,3-b]pyridin-3-ylidenemethyl]-4-methyl-1H-pyrrole-2-carboxylic acid (2-morpholin-4-yl-ethyl)-amide

HRID 397381

반응식

HRID 397381 반응식
[N:1]1([CH2:7][CH2:8][NH:9][C:10]([C:12]2[NH:13][C:14]([CH:18]=[C:19]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][C:26]=4Cl)[NH:21][C:20]3=[O:29])=[C:15]([CH3:17])[CH:16]=2)=[O:11])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:30][C:31]1[CH:32]=[C:33]([NH2:38])[CH:34]=[CH:35][C:36]=1[F:37].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>COCCOCCOC>[N:1]1([CH2:7][CH2:8][NH:9][C:10]([C:12]2[NH:13][C:14]([CH:18]=[C:19]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][C:26]=4[NH:38][C:33]4[CH:34]=[CH:35][C:36]([F:37])=[C:31]([Cl:30])[CH:32]=4)[NH:21][C:20]3=[O:29])=[C:15]([CH3:17])[CH:16]=2)=[O:11])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 97083-Chloro-4-fluoroanilineHCID 521998p-Toluenesulfonic acid monohydrateHCID 701609235-(4-chloro-2-oxo-1,2-dihydro-pyrrolo [2,3-b]pyridin-3-ylidenemethyl)-4-methyl-1H-pyrrole-2-carboxylic acid (2-morpholin-4-yl-ethyl)-amide

생성물 1

HCID 701605975-[4-(3-chloro-4-fluoro-phenylamino)-2-oxo-1,2-dihydro-pyrrolo [2,3-b]pyridin-3-ylidenemethyl]-4-methyl-1H-pyrrole-2-carboxylic acid (2-morpholin-4-yl-ethyl)-amide수율 28%

시약·촉매·용매 1

HCID 8150Diglyme용매

반응 조건

온도
185 °C

실험 절차

A mixture of 5-(4-chloro-2-oxo-1,2-dihydro-pyrrolo[2,3-b]pyridin-3-ylidenemethyl)-4-methyl-1H-pyrrole-2-carboxylic acid (2-morpholin-4-yl-ethyl)-amide (10 mg, 0.024 mmol), 3-chloro-4-fluoro-phenylamine (50 mg, 0.34 mmol), p-toluene sulfonic acid monohydrate (5 mg, 0.026 mmol) and 1 mL of 2-methoxyethyl ether was heated to 180-190° C. in a sealed tube for 6 hours, cooled to room temperature and concentrated. The residue was then purified using preparative TLC plates eluting with 10% methanol in dichloromethane to give 5-[4-(3-chloro-4-fluoro-phenylamino)-2-oxo-1,2-dihydro-pyrrolo[2,3-b]pyridin-3-ylidenemethyl]-4-methyl-1H-pyrrole-2-carboxylic acid (2-morpholin-4-yl-ethyl)-amide as an orange solid (yield is about 28%).

후처리

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was then purified
  4. washeluting with 10% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-a40e22106e934b398e3544574e60e86d
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610688B2

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