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

HRID 1947281ノート

反応式

HRID 1947281 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e22dbf4891d14d12ae82091a32c2833d
出典データセット
uspto-grants-2013_03
特許番号
US08399460B2

反応ノート

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