Hydrochloric Acid → Methyl 4-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-2-(cyclopropanecarbonyl)-4-oxobutanoate

HRID 1056292ノート

反応式

HRID 1056292 の反応式
Br[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[N:7]=[C:8]([NH:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:9]([CH3:15])=[N:10]2)=[O:4].[CH:21]1([C:24](=[O:30])[CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH2:23][CH2:22]1.C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C.C(Cl)Cl.O>[C:17]([NH:16][C:8]1[C:9]([CH3:15])=[N:10][C:11]2[C:6]([N:7]=1)=[C:5]([C:3](=[O:4])[CH2:2][CH:25]([C:24]([CH:21]1[CH2:23][CH2:22]1)=[O:30])[C:26]([O:28][CH3:29])=[O:27])[CH:14]=[CH:13][CH:12]=2)([CH3:20])([CH3:19])[CH3:18]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 101300163-Cyclopropyl-3-Oxopropionic Acid Methyl EsterHCID 897821422-Bromo-1-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)ethanone

生成物 1

HCID 89782054Methyl 4-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-2-(cyclopropanecarbonyl)-4-oxobutanoate

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 2-bromo-1-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)ethanone (606) (0.27 g, 0.803 mmol), methyl 3-cyclopropyl-3-oxopropanoate (Accela ChemBio, 0.114 mL, 0.803 mmol), K2CO3 (EMD, 0.333 g, 2.409 mmol), in DMF (3.21 ml) was combined and stirred overnight at RT. Reaction mixture was diluted with DCM and water. The aqueous layer was acidified with 1 N HCl solution and back extracted with DCM. The organic layers were combined and washed with water and brine to remove DMF. Volatile solvents were removed by rotovap. The product methyl 4-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-2-(cyclopropanecarbonyl)-4-oxobutanoate (418a) was advanced to next step. m/z (ESI, +ve) 398.1 (M+H).

後処理

  1. customReaction mixture
  2. extractionback extracted with DCM
  3. washwashed with water and brine
  4. customto remove DMF
  5. customVolatile solvents were removed by rotovap

出典と根拠

ORDレコード
ord-67e89136baae4291b4bc2e6ffd253075
出典データセット
uspto-grants-2016_07
特許番号
US09394297B2

反応ノート

読み込み中…