1-Methylpiperidin-3-amine → 6-Ethyl-5-[(1-methylpiperidin-3-yl)amino]-3-{[3-(methylsulfonyl)phenyl]amino}pyrazine-2-carboxamide

HRID 869273노트

반응식

HRID 869273 반응식
Cl[C:2]1[N:3]=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:15]=2)[C:5]([C:10]([NH2:12])=[O:11])=[N:6][C:7]=1[CH2:8][CH3:9].[CH3:24][N:25]1[CH2:30][CH2:29][CH2:28][CH:27]([NH2:31])[CH2:26]1>CN1C(=O)CCC1>[CH2:8]([C:7]1[N:6]=[C:5]([C:10]([NH2:12])=[O:11])[C:4]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:15]=2)=[N:3][C:2]=1[NH:31][CH:27]1[CH2:28][CH2:29][CH2:30][N:25]([CH3:24])[CH2:26]1)[CH3:9]

참가 물질

4

반응물 2

HCID 38609711-Methylpiperidin-3-amineHCID 866620465-Chloro-6-ethyl-3-{[3-(methylsulfonyl)phenyl]amino}pyrazine-2-carboxamide

생성물 1

HCID 666430756-Ethyl-5-[(1-methylpiperidin-3-yl)amino]-3-{[3-(methylsulfonyl)phenyl]amino}pyrazine-2-carboxamide수율 22.4%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
190 °C

실험 절차

A mixture of 5-chloro-6-ethyl-3-{[3-(methylsulfonyl)phenyl]amino}pyrazine-2-carboxamide (Preparation Example 353) (8.8 mg), 1-methyl-piperidin-3-ylamine (8.0 mg) and NMP (0.5 mL) was heated at 190° C. for 30 minutes using a microwave reaction system. After the reaction liquid was cooled, the organic layer was distilled off under reduced pressure, and the residue was separated and purified by HPLC (column: SunFire® C18, 5 μm, 19 mm×100 mm, solvent: MeOH/0.1% HCOOH—H2O=10/90 (0 min)-10/90 (1 min)-95/5 (9 min)-95/5 (12 min), flow rate: 25 mL/min) to give (6-ethyl-5-[(1-methylpiperidin-3-yl)amino]-3-{[3-(methylsulfonyl)phenyl]amino}pyrazine-2-carboxamide (2.4 mg).

후처리

  1. customa microwave reaction system
  2. customAfter the reaction liquid
  3. temperaturewas cooled
  4. distillationthe organic layer was distilled off under reduced pressure
  5. customthe residue was separated
  6. custompurified by HPLC (column: SunFire® C18, 5 μm, 19 mm×100 mm, solvent: MeOH/0.1% HCOOH—H2O=10/90 (0 min)-10/90 (1 min)-95/5 (9 min)-95/5 (12 min), flow rate: 25 mL/min)

출처 및 근거

ORD 기록
ord-a7ca1edd69e0403889dc3b47f4a94347
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969336B2

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