Hydrochloric Acid → (5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine hydrochloride

HRID 2204560ノート

反応式

HRID 2204560 の反応式
[N:1]([CH2:4][C:5]1[N:6]=[C:7]2[CH:13]=[CH:12][N:11]([S:14]([C:17]3[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[C:8]2=[N:9][CH:10]=1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[ClH:43].CO>C1COCC1.O>[ClH:43].[S:14]([N:11]1[C:8]2=[N:9][CH:10]=[C:5]([CH2:4][NH2:1])[N:6]=[C:7]2[CH:13]=[CH:12]1)([C:17]1[CH:18]=[CH:19][C:20]([CH3:21])=[CH:22][CH:23]=1)(=[O:15])=[O:16]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11776TriphenylphosphineHCID 866371832-(azidomethyl)-5-tosyl-5H-pyrrolo[2,3-b]pyrazine

生成物 1

HCID 67068339(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine hydrochloride収率 95.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
45 °C

実験手順

To a solution of 2-(azidomethyl)-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (32.6 g, 99.0 mmol) in THF (100 mL) and water (50 mL) was added Ph3P (31.3 g, 119 mmol). The reaction mixture was heated to about 45° C. for about 16 h. The mixture was allowed to cool to ambient temperature followed by removal of THF under reduced pressure. The mixture was partitioned between EtOAc (500 mL) and brine (250 mL), dried over anhydrous Na2SO4, and filtered. The filtrate was diluted with EtOAc to 1 L total volume. To the rapidly stirring solution was added drop-wise 4N HCl (4N in dioxane, 30.0 mL, 120 mmol) resulting in formation of a tan precipitate. MeOH (10 mL) was added and the mixture was filtered after about 15 min. The precipitate was triturated with Et2O (1000 mL) for about 10 min, filtered, and washed with Et2O (500 mL) to provide (5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine hydrochloride (32.0 g, 90%) as a tan solid: LC/MS (Table 2, Method a) Rt=1.44 min; MS m/z: 303 (M+H)+.

後処理

  1. temperatureto cool to ambient temperature
  2. customfollowed by removal of THF under reduced pressure
  3. customThe mixture was partitioned between EtOAc (500 mL) and brine (250 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. additionThe filtrate was diluted with EtOAc to 1 L total volume
  7. customresulting in formation of a tan precipitate
  8. filtrationthe mixture was filtered after about 15 min
  9. customThe precipitate was triturated with Et2O (1000 mL) for about 10 min
  10. filtrationfiltered
  11. washwashed with Et2O (500 mL)

出典と根拠

ORDレコード
ord-4854b49111bd48dba46c0d6c619e33b4
出典データセット
uspto-grants-2016_06
特許番号
US09365579B2

反応ノート

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