Diisopropylethylamine → 8-(2,6-dichloro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid [1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-amide

HRID 1189745ノート

反応式

HRID 1189745 の反応式
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl: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.[CH3:26][Si:27]([CH3:39])([CH3:38])[CH2:28][CH2:29][O:30][CH2:31][N:32]1[CH:36]=[CH:35][N:34]=[C:33]1[NH2:37].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>[CH3:26][Si:27]([CH3:39])([CH3:38])[CH2:28][CH2:29][O:30][CH2:31][N:32]1[CH:36]=[CH:35][N:34]=[C:33]1[NH:37][C:23]([C:16]1[C:17]2[N:18]=[CH:19][CH:20]=[N:21][C:22]=2[C:13]([C:3]2[C:4]([Cl:12])=[C:5]([O:10][CH3:11])[CH:6]=[C:7]([O:8][CH3:9])[C:2]=2[Cl:1])=[CH:14][CH:15]=1)=[O:24]

参加物

8

反応物 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 592928388-(2,6-Dichloro-3,5-dimethoxy-phenyl)quinoxaline-5-carboxylic acidHCID 669145481-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-ylamine

生成物 1

HCID 866411408-(2,6-dichloro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid [1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-amide収率 85.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 8-(2,6-dichloro-3,5-dimethoxy-phenyl)quinoxaline-5-carboxylic acid (Step 1.1) (0.400 g, 1.06 mmol), 1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-ylamine (Step 14.2) (0.270 g, 1.27 mmol, 1.2 equiv), TBTU (408 mg, 1.27 mmol, 1.2 equiv), DIEA (0.74 mL, 4.23 mmol, 4.0 equiv) in DMF (5 mL) was stirred for 2 h at rt, diluted with EtOAc and H2O, and extracted with EtOAc.washed with a saturated aqueous solution of NaHCO3, H2O, and brine. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (DCM/MeOH, 95:5) to afford 0.518 g of the title compound as a yellow foam: ES-MS: 573.8/575.8 [M+H]+; tR=5.03 min (System 1); Rf=0.19 (DCM2/MeOH, 95:5).

後処理

  1. extractionextracted with EtOAc
  2. washwashed with a saturated aqueous solution of NaHCO3, H2O, and brine
  3. washThe organic phase was washed with H2O and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (DCM/MeOH, 95:5)

出典と根拠

ORDレコード
ord-f0d7cfafb2f945efaa029f981b7a7d41
出典データセット
uspto-grants-2014_03
特許番号
US08674099B2

反応ノート

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