Diisopropylethylamine → HCID 178493498、化合物

HRID 1189907ノート

反応式

HRID 1189907 の反応式
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([F:12])[C:3]=1[C:13]1[C:22]2[N:21]=[CH:20][CH:19]=[N:18][C:17]=2[C:16]([C:23](O)=[O:24])=[CH:15][CH:14]=1.C(OC([N:33]1[CH:37]=[C:36]([CH:38](OCC)[O:39]CC)[N:35]=[C:34]1[NH2:45])=O)(C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O.O>[CH:38]([C:36]1[N:35]=[C:34]([NH:45][C:23]([C:16]2[C:17]3[N:18]=[CH:19][CH:20]=[N:21][C:22]=3[C:13]([C:3]3[C:4]([F:12])=[C:5]([O:10][CH3:11])[CH:6]=[C:7]([O:8][CH3:9])[C:2]=3[F:1])=[CH:14][CH:15]=2)=[O:24])[NH:33][CH:37]=1)=[O:39]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 592928212-Amino-4-diethoxymethyl-imidazole-1-carboxylic acid tert-butyl esterHCID 592928348-(2,6-Difluoro-3,5-dimethoxy-phenyl)quinoxaline-5-carboxylic acid

生成物 1

HCID 178493498HCID 178493498、化合物収率 68.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 22728543Water ethylacetate溶媒

実験手順

A mixture of 8-(2,6-difluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid (200 mg, 0.578 mmol) (Step 185.1), 2-amino-4-diethoxymethyl-imidazole-1-carboxylic acid tert-butyl ester (198 mg, 0.693 mmol, 1.2 equiv) (Step 179.8), TBTU (223 mg, 0.693 mmol, 1.2 equiv), DIEA (74.7 mg, 0.578 mmol) in DMF (4 mL) was stirred for 18 h at rt. The reaction mixture was diluted in EtOAc/H2O and extracted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The resulting yellow foam (405 mg) was dissolved in acetone (5 mL) and H2O (3 mL) and treated with PPTS (30 mg). The reaction mixture was heated to 50° C., stirred for 2 h, allowed to cool to rt and diluted with EtOAc/H2O. The resulting yellow precipitate was collected by vacuum filtration and dried to provide 174 mg of the title compound: ES-MS: 440 [M+H]+; tR=3.89 min (System 1).

後処理

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with H2O and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe resulting yellow foam (405 mg) was dissolved in acetone (5 mL)
  7. additionH2O (3 mL) and treated with PPTS (30 mg)
  8. temperatureThe reaction mixture was heated to 50° C.
  9. stirringstirred for 2 h
  10. temperatureto cool to rt
  11. additiondiluted with EtOAc/H2O
  12. filtrationThe resulting yellow precipitate was collected by vacuum filtration
  13. customdried

出典と根拠

ORDレコード
ord-5a19e4936b6e417c9e8bd8f6d5bf6436
出典データセット
uspto-grants-2014_03
特許番号
US08674099B2

反応ノート

読み込み中…