1-Butanol → 8-[5-(1-Hydroxy-1-methylethyl)pyridin-3-yl]-1-[(2S)-2-methoxypropyl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one fumarate

HRID 244600ノート

反応式

HRID 244600 の反応式
[OH:1][C:2]([C:5]1[CH:6]=[C:7]([C:11]2[CH:20]=[CH:19][C:18]3[N:17]=[CH:16][C:15]4[N:21]([CH3:30])[C:22](=[O:29])[N:23]([CH2:24][C@@H:25]([O:27][CH3:28])[CH3:26])[C:14]=4[C:13]=3[CH:12]=2)[CH:8]=[N:9][CH:10]=1)([CH3:4])[CH3:3].C(O)CCC.[C:36]([OH:43])(=[O:42])/[CH:37]=[CH:38]/[C:39]([OH:41])=[O:40]>CCCCCCC>[C:36]([OH:43])(=[O:42])/[CH:37]=[CH:38]/[C:39]([OH:41])=[O:40].[OH:1][C:2]([C:5]1[CH:6]=[C:7]([C:11]2[CH:20]=[CH:19][C:18]3[N:17]=[CH:16][C:15]4[N:21]([CH3:30])[C:22](=[O:29])[N:23]([CH2:24][C@@H:25]([O:27][CH3:28])[CH3:26])[C:14]=4[C:13]=3[CH:12]=2)[CH:8]=[N:9][CH:10]=1)([CH3:3])[CH3:4]

参加物

5

反応物 3

HCID 2631-Butanol2 回HCID 444972Fumaric Acid2 回HCID 57519748Samotolisib

生成物 1

HCID 681085528-[5-(1-Hydroxy-1-methylethyl)pyridin-3-yl]-1-[(2S)-2-methoxypropyl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one fumarate

試薬・触媒・溶媒 1

HCID 8900Heptane溶媒2 回

反応条件

温度
90 °C

実験手順

Example 5 can be prepared as by adding free base 8-[5-(1-hydroxy-1-methylethyl)pyridin-3-yl]-1-[(2S)-2-methoxypropyl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one (60.2 mg) to 1-butanol (0.5 mL) and then add 21.9 mg fumaric acid. Add heptane (5×0.5 mL), which produces thick white slurry, and stir at 90° C./500 rpm. Vacuum filter and dry under nitrogen. Solids are lost during recovery from filtration, though sufficient for XRD. Additional crystalline fumarate salt is prepared by adding free base (101.0 mg) to 1-butanol (0.5 mL) and then add 34 mg fumaric acid. Add heptane (6×0.5 mL) and crystalline seeds of the fumarate salt from first preparation and stir the mixture at 90° C./500 rpm for 1 hour. Recover the solids by vacuum filtration and dry the solids under nitrogen. Further dry the solids in a vacuum oven (65° C.) overnight to provide the title compound.

後処理

  1. customExample 5 can be prepared as
  2. filtrationVacuum filter
  3. customdry under nitrogen
  4. filtrationSolids are lost during recovery from filtration
  5. stirringstir the mixture at 90° C./500 rpm for 1 hour
  6. customRecover the solids
  7. filtrationby vacuum filtration
  8. customdry the solids under nitrogen
  9. customFurther dry the solids in a vacuum oven (65° C.) overnight

出典と根拠

ORDレコード
ord-a29cfa1c3e8840529cfc75fcc71f14da
出典データセット
uspto-grants-2014_02
特許番号
US08658668B2

反応ノート

読み込み中…