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

HRID 1056292노트

반응식

HRID 1056292 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-67e89136baae4291b4bc2e6ffd253075
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394297B2

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