Diisopropylamine → 4-[2-Fluoro-4-(2-pyridin-3-yl-benzoylamino)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 2196183ノート

反応式

HRID 2196183 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][C:15]=2[F:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]2[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=2[C:30](O)=[O:31])[CH:23]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(NC(C)C)(C)C>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:30](=[O:31])[C:29]3[CH:33]=[CH:34][CH:35]=[CH:36][C:28]=3[C:24]3[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=3)=[CH:16][C:15]=2[F:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 4

HCID 7912DiisopropylamineHCID 27605052-(Pyridin-3-yl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 162036301,1-Dimethylethyl 4-(4-amino-2-fluorophenyl)-1-piperazinecarboxylate

生成物 1

HCID 669318584-[2-Fluoro-4-(2-pyridin-3-yl-benzoylamino)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 4-(4-Amino-2-fluoro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (1.00 g, 3.4 mmol) and 2-pyrid-3-yl benzoic acid (0.70 g, 3.7 mmol) in DMF (10 mL) was added HATU (1.42 g, 3.7 mmol) and diisopropylamine (0.65 mL, 3.7 mmol). After stirring at room temperature for 18 h, the reaction mixture was diluted with EtOAc (100 mL) and washed with H2O (4×50 mL). The organic extracts were combined, dried (Na2SO4), and the solvent was evaporated under reduced pressure. Chromatography of the resulting residue (SiO2: EtOAc:Hex) yielded 4-[2-fluoro-4-(2-pyridin-3-yl-benzoylamino)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester which was further dissolved in MeOH (20 mL) and 4N HCl in dioxanes. After stirring for 5 h, the reaction mixture was concentrated down, neutralized with 1N NaOH, and extracted with EtOAc (3×75mL). The organic extracts were combined, dried (Na2SO4), and the solvent was evaporated under reduced pressure to yield the title compound.

後処理

  1. washwashed with H2O (4×50 mL)
  2. dry with materialdried (Na2SO4)
  3. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-7d22b536dda2404ba9bff137375abc94
出典データセット
uspto-grants-2012_12
特許番号
US08338426B2

反応ノート

読み込み中…