Hydrochloric Acid → (3S)-3-({4-[2-fluoro-4-(7-quinolinyl)phenyl]-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl}methyl)-N,N-dimethyl-1-pyrrolidinecarboxamide

HRID 2405437ノート

反応式

HRID 2405437 の反応式
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[CH:13][CH:14]=[N:15]3)=[CH:10][CH:9]=2)[CH:5]=[CH:4][C:3]=1[N:18]1[C:22](=[O:23])[NH:21][N:20]=[C:19]1[CH2:24][C@@H:25]1[CH2:29][CH2:28][N:27]([C:30]([O:32]C(C)(C)C)=O)[CH2:26]1.Cl.[CH:38]([N:41](CC)[CH:42](C)C)(C)C.CNN(NC)C(Cl)=O.[NH4+].[Cl-]>O1CCOCC1.ClCCl>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[CH:13][CH:14]=[N:15]3)=[CH:10][CH:9]=2)[CH:5]=[CH:4][C:3]=1[N:18]1[C:22](=[O:23])[NH:21][N:20]=[C:19]1[CH2:24][C@@H:25]1[CH2:29][CH2:28][N:27]([C:30]([N:41]([CH3:42])[CH3:38])=[O:32])[CH2:26]1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 673549061,1-dimethylethyl (3S)-3-({4-[2-fluoro-4-(7-quinolinyl)phenyl]-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl}methyl)-1-pyrrolidinecarboxylateHCID 86674832N,N-dimethylaminocarbamoyl chloride

生成物 1

HCID 67380101(3S)-3-({4-[2-fluoro-4-(7-quinolinyl)phenyl]-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl}methyl)-N,N-dimethyl-1-pyrrolidinecarboxamide

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒3 回HCID 312751,4-Dioxane溶媒

実験手順

Into a 8 mL screwcap vial was placed 1,1-dimethylethyl (3S)-3-({4-[2-fluoro-4-(7-quinolinyl)phenyl]-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl}methyl)-1-pyrrolidinecarboxylate (0.161 mmol). Added to the vial was 4N HCl in dioxane (1 mL). The reaction mixture was capped and stirred at room temperature for 2 h. The solution was concentrated in vacuo. Added to the vial were dichloromethane (1 mL) and N,N-diisopropylethylamine (0.573 mmol). In a separate vial, N,N-dimethylaminocarbamoyl chloride (0.161 mmol) was dissolved in 1 mL dichloromethane and added to the starting material dropwise via pipette. The vial was capped and the reaction was stirred at room temperature for 2 h. An extra 2 mL dichloromethane was added to the vial, followed by the addition of saturated aq NH4Cl (2 mL). The vial was capped and lightly agitated for 1 min. The organic layer was separated, filtered through a plug of sodium sulfate, and concentrated in vacuo. Reverse phase HPLC (10-65% acetonitrile/water+0.1% NH4OH) was utilized in purifying the title compound (44 mg, 59%). MS(ES)+ m/e 461.2 [M+H]+.

後処理

  1. additionAdded to the vial
  2. customThe reaction mixture was capped
  3. concentrationThe solution was concentrated in vacuo
  4. additionAdded to the
  5. additionadded to the starting material dropwise via pipette
  6. customThe vial was capped
  7. stirringthe reaction was stirred at room temperature for 2 h
  8. customThe vial was capped
  9. stirringlightly agitated for 1 min
  10. customThe organic layer was separated
  11. filtrationfiltered through a plug of sodium sulfate
  12. concentrationconcentrated in vacuo
  13. customin purifying the title compound (44 mg, 59%)

出典と根拠

ORDレコード
ord-8eddb543177e4d71833e822417a24caa
出典データセット
uspto-grants-2014_08
特許番号
US08802864B2

反応ノート

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