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

HRID 869273ノート

反応式

HRID 869273 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
190 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-a7ca1edd69e0403889dc3b47f4a94347
出典データセット
uspto-grants-2015_03
特許番号
US08969336B2

反応ノート

読み込み中…