Pyrrolidine → 8-(1-hydroxyethyl)-2-morpholino-6-(pyrrolidine-1-carbonyl)-4H-chromen-4-one

HRID 572786ノート

反応式

HRID 572786 の反応式
[B-](F)(F)(F)F.CN(C(O[N:14]1[C:19](=O)[CH2:18][CH2:17][C:15]1=O)=[N+](C)C)C.[OH:21][CH:22]([C:24]1[CH:25]=[C:26]([C:41](O)=[O:42])[CH:27]=[C:28]2[C:33]=1[O:32][C:31]([N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1)=[CH:30][C:29]2=[O:40])[CH3:23].C(N(C(C)C)C(C)C)C.N1CCCC1>C(Cl)Cl>[OH:21][CH:22]([C:24]1[CH:25]=[C:26]([C:41]([N:14]2[CH2:15][CH2:17][CH2:18][CH2:19]2)=[O:42])[CH:27]=[C:28]2[C:33]=1[O:32][C:31]([N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1)=[CH:30][C:29]2=[O:40])[CH3:23]

参加物

6

反応物 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 582349808-(1-hydroxyethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid

生成物 1

HCID 582350218-(1-hydroxyethyl)-2-morpholino-6-(pyrrolidine-1-carbonyl)-4H-chromen-4-one収率 80.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

2-(2,5-dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate (3.34 g, 11.09 mmol) at 25° C. was added portionwise to 8-(1-hydroxyethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (1.77 g, 5.54 mmol) and N-ethyl-N-isopropylpropan-2-amine (2.028 mL, 11.64 mmol) suspended in DCM (15 mL) under nitrogen. The resulting mixture was stirred at 25° C. for 5 hrs. Pyrrolidine (1.388 mL, 16.63 mmol) was then added to the mixture and the resulting mixture was stirred at 25° C. overnight. The mixture was poured onto a silica gel column and purified by flash chromatography eluting with 2 to 7% methanolic ammonia (7 N) in DCM. The solvent was evaporated to dryness, the residue was triturated in ethylacetate (10 mL), collected by filtration and dried to afford 8-(1-hydroxyethyl)-2-morpholino-6-(pyrrolidine-1-carbonyl)-4H-chromen-4-one (1.66 g, 80%) as a beige solid. Mass Spectrum: M+H+ 373.

後処理

  1. stirringthe resulting mixture was stirred at 25° C. overnight
  2. additionThe mixture was poured onto a silica gel column
  3. custompurified by flash chromatography
  4. washeluting with 2 to 7% methanolic ammonia (7 N) in DCM
  5. customThe solvent was evaporated to dryness
  6. customthe residue was triturated in ethylacetate (10 mL)
  7. filtrationcollected by filtration
  8. customdried

出典と根拠

ORDレコード
ord-b66787a6d6dd4528972d2dd71474a7c7
出典データセット
uspto-grants-2015_05
特許番号
US09029374B2

反応ノート

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