N,N-Dimethylethylenediamine → 8-acetyl-N-(2-(dimethylamino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxamide

HRID 1187169노트

반응식

HRID 1187169 반응식
[C:1]([C:4]1[CH:5]=[C:6]([C:21](O)=[O:22])[CH:7]=[C:8]2[C:13]=1[O:12][C:11]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=[CH:10][C:9]2=[O:20])(=[O:3])[CH3:2].CCN(C(C)C)C(C)C.[B-](F)(F)(F)F.CN(C(ON1C(=O)CCC1=O)=[N+](C)C)C.[CH3:53][N:54]([CH3:58])[CH2:55][CH2:56][NH2:57]>C(Cl)Cl>[C:1]([C:4]1[CH:5]=[C:6]([C:21]([NH:57][CH2:56][CH2:55][N:54]([CH3:58])[CH3:53])=[O:22])[CH:7]=[C:8]2[C:13]=1[O:12][C:11]([N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1)=[CH:10][C:9]2=[O:20])(=[O:3])[CH3:2]

참가 물질

6

반응물 4

HCID 66053N,N-DimethylethylenediamineHCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 582349818-acetyl-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid

생성물 1

HCID 582349798-acetyl-N-(2-(dimethylamino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxamide수율 61.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a suspension of 8-acetyl-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (470 mg, 1.48 mmol) in DCM (10 mL) at room temperature, were added to DIPEA (0.284 mL, 1.63 mmol) and TSTU (491 mg, 1.63 mmol). The mixture was stirred for 15 minutes, N1,N1-dimethylethane-1,2-diamine (0.171 mL, 1.56 mmol) was added stirring was maintained for an additional hour. The mixture was adsorbed on silica gel and purified by flash chromatography on silica gel eluting with 5 to 10% methanol in DCM then with 10% methanolic ammonia (7 N) in DCM. The solvent was evaporated to dryness to afford 8-acetyl-N-(2-(dimethylamino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxamide (352 mg, 61.3%) as a beige solid. Mass Spectrum: M+H+ 388.

후처리

  1. stirringstirring
  2. temperaturewas maintained for an additional hour
  3. custompurified by flash chromatography on silica gel eluting with 5 to 10% methanol in DCM
  4. customThe solvent was evaporated to dryness

출처 및 근거

ORD 기록
ord-a851fe12a63e4ec29cf61a07d98a6d57
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673906B2

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