N-bromobutanimide → 3-Bromo-1-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine

HRID 1628107ノート

反応式

HRID 1628107 の反応式
[CH:1]1([C:7]2[N:11]3[C:12]4[CH:18]=[CH:17][N:16]([S:19]([C:22]5[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=5)(=[O:21])=[O:20])[C:13]=4[N:14]=[CH:15][C:10]3=[CH:9][N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C(=O)N([Br:36])C(=O)C1>C1COCC1.CCOC(C)=O.C([O-])(O)=O.[Na+]>[Br:36][C:9]1[N:8]=[C:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[N:11]2[C:12]3[CH:18]=[CH:17][N:16]([S:19]([C:22]4[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=4)(=[O:20])=[O:21])[C:13]=3[N:14]=[CH:15][C:10]=12

参加物

6

反応物 2

HCID 67184N-bromobutanimideHCID 580099171-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine

生成物 1

HCID 583822553-Bromo-1-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine収率 84.9%

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of 1-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.27 g, 0.672 mmol) in THF (10 mL) at about 0° C. was added a solution of NBS (0.12 g, 0.672 mmol) in THF (2 mL). After about 30 min, the mixture was diluted with EtOAc (20 mL) and saturated aqueous NaHCO3 (20 mL). The organic layer was separated, concentrated in vacuo, and purified by chromatography on silica gel (40 g) eluting with EtOAc:DCM:heptane (1:1:2) to provide 3-Bromo-1-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.27 g, 83%). LC/MS (Table 2, Method a) Rt=3.12 min; MS m/z 473 (M+H)+.

後処理

  1. customThe organic layer was separated
  2. concentrationconcentrated in vacuo
  3. custompurified by chromatography on silica gel (40 g)
  4. washeluting with EtOAc:DCM:heptane (1:1:2)

出典と根拠

ORDレコード
ord-fa6c9b3150354fc0b13df59827b08d1a
出典データセット
uspto-grants-2014_07
特許番号
US08785639B2

反応ノート

読み込み中…