Trifluoroacetic acid → HCID 178493776、化合物

HRID 606772ノート

反応式

HRID 606772 の反応式
C(O[C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[NH:19][N:18]=[C:17]([CH3:20])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O.Cl.[CH3:35][O:36][C:37]1[CH:45]=[N:44][C:43]([N:46]2[CH:50]=[C:49]([CH3:51])[N:48]=[N:47]2)=[C:42]2[C:38]=1[C:39]([C:52](=[O:56])C(O)=O)=[CH:40][NH:41]2.C(N(CC)CC)(C)C.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1>C(Cl)Cl>[C:21]1([C:14](=[C:11]2[CH2:12][CH2:13][N:8]([C:6](=[O:7])[C:52]([C:39]3[C:38]4[C:42](=[C:43]([N:46]5[CH:50]=[C:49]([CH3:51])[N:48]=[N:47]5)[N:44]=[CH:45][C:37]=4[O:36][CH3:35])[NH:41][CH:40]=3)=[O:56])[CH2:9][CH2:10]2)[C:15]2[NH:19][N:18]=[C:17]([CH3:20])[CH:16]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

7

反応物 5

HCID 6422Trifluoroacetic acidHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 521913N,N-Diethyl-2-propanamineHCID 670465684-Methoxy-7-(4-methyl-1,2,3-triazol-1-yl)-6-azaindol-3-yl-oxoacetic acid hydrochloride saltHCID 178423825HCID 178423825、化合物

生成物 1

HCID 178493776HCID 178493776、化合物収率 44.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 4-[1-phenyl-1-(3-methylpyrazol-5-yl)methylene]piperidine-1-carboxylic acid tert-butyl ester (0.0190 g, 0.0538 mmol) in CH2Cl2 (1 mL) was added TFA (0.4 mL) and the mixture was stirred at rt for 30 min. The solvent was then removed in vacuo and the material was dissolved in CHCl3 (2 mL). To this solution was added 4-methoxy-7-(4-methyl-1,2,3-triazol-1-yl)-6-azaindol-3-yl-oxoacetic acid hydrochloride salt (0.0187 g, 0.0621 mmol) and iPrNEt2 (0.050 mL, 0.287 mmol), followed by BOP-Cl (0.0221 g, 0.868 mmol). The mixture was allowed to stir at rt for 2 h and then the solvent was removed in vacuo. The resulting residue was diluted with H2O and extracted with EtOAc (×3). The combined organic layers were washed (H2O, brine), dried (Na2SO4) and concentrated, and the residue was purified by preparative HPLC (NH4OAc) to give the title compound (0.0128 g, 44%) as a colorless solid:

後処理

  1. customThe solvent was then removed in vacuo
  2. dissolutionthe material was dissolved in CHCl3 (2 mL)
  3. stirringto stir at rt for 2 h
  4. customthe solvent was removed in vacuo
  5. additionThe resulting residue was diluted with H2O
  6. extractionextracted with EtOAc (×3)
  7. washThe combined organic layers were washed (H2O, brine)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customthe residue was purified by preparative HPLC (NH4OAc)

出典と根拠

ORDレコード
ord-d0dbf3df1e2d4cb5bda834e92a42ed63
出典データセット
uspto-grants-2011_03
特許番号
US07915283B2

反応ノート

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