Pyrrolidine → 2-Amino-7-(4-fluoro-phenyl)-4-methyl-7,8-dihydro-6H-quinazolin-5-one

HRID 2046466ノート

反応式

HRID 2046466 の反応式
[C:1]([CH:4]1[C:9](=[O:10])[CH2:8][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH2:6][C:5]1=O)(=O)[CH3:2].N1CCCC1.C(=O)(O)O.[NH2:28][C:29]([NH2:31])=[NH:30]>C(Cl)(Cl)Cl.O1CCOCC1>[NH2:31][C:29]1[N:30]=[C:1]([CH3:2])[C:4]2[C:9](=[O:10])[CH2:8][CH:7]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[CH2:6][C:5]=2[N:28]=1

参加物

6

反応物 3

HCID 31268PyrrolidineHCID 286947Carbonic acid-guanidine (1:1)HCID 529508832-Acetyl-5-(4-fluoro-phenyl)cyclohexane-1,3-dione2 回

生成物 1

HCID 172212082-Amino-7-(4-fluoro-phenyl)-4-methyl-7,8-dihydro-6H-quinazolin-5-one

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a stirred solution of 2-acetyl-5-(4-fluoro-phenyl)-cyclohexane-1,3-dione (200 mg, 0.80 mmol) from stage 1, in chloroform was added pyrrolidine (68 mg, 0.96 mmol). The reaction mixture was stirred at ambient temperature and monitored by TLC until complete disappearance of 2-acetyl-5-(4-fluoro-phenyl)cyclohexane-1,3-dione. The reaction mixture was washed with water (10 ml) and the solvent was removed under reduced pressure to give a solid m=229 mg, mass spectrum (ES-MS (+ve)) 302 [MH]+, Retention time 1.44 min, 100% UV. To a stirred solution of this solid (229 mg, 0.76 mmol) in dioxane (2.5 ml) was added guanidine carbonate (504 mg, 2.8 mmol) and the mixture heated at 100° C. and stirred for 16 h. 1,4-Dioxane was removed by evaporation under reduced pressure, water (5 ml) was added and the resulting precipitate was filtered, washed with water and heptane and air dried.

後処理

  1. washThe reaction mixture was washed with water (10 ml)
  2. customthe solvent was removed under reduced pressure
  3. customto give a solid m=229 mg, mass spectrum (ES-MS (+ve)) 302 [MH]+, Retention time 1.44 min, 100% UV
  4. temperaturethe mixture heated at 100° C.
  5. stirringstirred for 16 h
  6. custom1,4-Dioxane was removed by evaporation under reduced pressure, water (5 ml)
  7. additionwas added
  8. filtrationthe resulting precipitate was filtered
  9. washwashed with water and heptane and air
  10. customdried

出典と根拠

ORDレコード
ord-0054e2e1045a47d5bf47ff40034835b9
出典データセット
uspto-grants-2013_11
特許番号
US08592430B2

反応ノート

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