Acetic Acid → (R)-2-(2-amino-5-fluorophenylamino)-6-chloro-9-(8-fluorochroman-4-yl)-7H-purin-8(9H)-one

HRID 2074178ノート

反応式

HRID 2074178 の反応式
[Cl:1][C:2]1[N:10]=[C:9]([NH:11][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[N+:19]([O-])=O)[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:33])[N:6]2[C@H:22]1[C:31]2[C:26](=[C:27]([F:32])[CH:28]=[CH:29][CH:30]=2)[O:25][CH2:24][CH2:23]1.C(O)(=O)C.O.[OH-].[NH4+]>[Fe].C(O)C>[NH2:19][C:13]1[CH:14]=[CH:15][C:16]([F:18])=[CH:17][C:12]=1[NH:11][C:9]1[N:8]=[C:7]2[C:3]([NH:4][C:5](=[O:33])[N:6]2[C@H:22]2[C:31]3[C:26](=[C:27]([F:32])[CH:28]=[CH:29][CH:30]=3)[O:25][CH2:24][CH2:23]2)=[C:2]([Cl:1])[N:10]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 962WaterHCID 14923Ammonium HydroxideHCID 57612627(R)-6-chloro-2-(5-fluoro-2-nitrophenylamino)-9-(8-fluorochroman-4-yl)-7H-purin-8(9H)-one

生成物 1

HCID 86622939(R)-2-(2-amino-5-fluorophenylamino)-6-chloro-9-(8-fluorochroman-4-yl)-7H-purin-8(9H)-one

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

反応条件

温度
90 °C

実験手順

To a round bottom flask containing (R)-6-chloro-2-(5-fluoro-2-nitrophenylamino)-9-(8-fluorochroman-4-yl)-7H-purin-8(9H)-one (310 mg, 0.65 mmol) was added glacial acetic acid (15 mL), water (37.5 mL) and ethanol (75 mL), followed by iron powder (370 mg, 6.5 mmol, 10 equiv.) and the resulting mixture heated at 90° C. for 15 min (HPLC monitoring). The reaction mixture was left to cool down to room temperature, concentrated ammonium hydroxide solution (32 mL) was added to bring the pH to basic, and the mixture was stirred for 10 min. The aqueous layer was extracted with ethyl acetate (5×100 mL), the combined organic layers were washed with brine, dried (anhydrous Na2SO4), and the solvent removed in vacuo to give the desired product as a pink solid (yield quantitative). This material was used in the next step without further purification. MS (EI) m/z 445.2 (MH)+.

後処理

  1. waitThe reaction mixture was left
  2. temperatureto cool down to room temperature
  3. extractionThe aqueous layer was extracted with ethyl acetate (5×100 mL)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried (anhydrous Na2SO4)
  6. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-0f2b1a73dfa2469ca225c61463cc8527
出典データセット
uspto-grants-2011_04
特許番号
US07919490B2

反応ノート

読み込み中…