Triethylamine → 8-(2,6-Dichloro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid [4-(4-ethyl-piperazin-1-yl)-phenyl]-amide

HRID 2391757

反応式

HRID 2391757 の反応式
CCCP(=O)=O.[Cl:7][C:8]1[C:13]([O:14][CH3:15])=[CH:12][C:11]([O:16][CH3:17])=[C:10]([Cl:18])[C:9]=1[C:19]1[C:28]2[N:27]=[CH:26][CH:25]=[N:24][C:23]=2[C:22]([C:29]([OH:31])=O)=[CH:21][CH:20]=1.[CH2:32]([N:34]1[CH2:39][CH2:38][N:37]([C:40]2[CH:46]=[CH:45][C:43]([NH2:44])=[CH:42][CH:41]=2)[CH2:36][CH2:35]1)[CH3:33].CCN(CC)CC>CN(C1C=CN=CC=1)C.CN(C=O)C.CCOC(C)=O.O>[CH2:32]([N:34]1[CH2:35][CH2:36][N:37]([C:40]2[CH:46]=[CH:45][C:43]([NH:44][C:29]([C:22]3[C:23]4[N:24]=[CH:25][CH:26]=[N:27][C:28]=4[C:19]([C:9]4[C:8]([Cl:7])=[C:13]([O:14][CH3:15])[CH:12]=[C:11]([O:16][CH3:17])[C:10]=4[Cl:18])=[CH:20][CH:21]=3)=[O:31])=[CH:42][CH:41]=2)[CH2:38][CH2:39]1)[CH3:33]

参加物

9

反応物 4

HCID 8471TriethylamineHCID 9367384-(4-Ethylpiperazin-1-yl)anilineHCID 16167369Propylphosphoric anhydrideHCID 592928388-(2,6-Dichloro-3,5-dimethoxy-phenyl)quinoxaline-5-carboxylic acid

生成物 1

HCID 445135288-(2,6-Dichloro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid [4-(4-ethyl-piperazin-1-yl)-phenyl]-amide

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of propylphosphonic anhydride (50% in DMF, 0.31 mL, 0.53 mmol, 2 equiv), 8-(2,6-dichloro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid (100 mg, 0.26 mmol) (Step 1.1), 4-(4-ethylpiperazin-1-yl)-aniline (Step 1.9) (65 mg, 0.32 mmol, 1.2 equiv), DMAP (2 mg), and Et3N (0.37 mL, 2.65 mmol, 10 equiv) in DMF (2.0 mL), was stirred for 18 h at rt, under an argon atmosphere. The reaction mixture was diluted with EtOAc and H2O. The aqueous layer was separated and extracted with EtOAc. The combined organic phase was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by trituration in Et2O to afford the title compound as a yellow solid: ES-MS: 565.9 [M+H]+; tR=4.26 min (System 1).

後処理

  1. customThe aqueous layer was separated
  2. extractionextracted with EtOAc
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by trituration in Et2O

出典と根拠

ORDレコード
ord-d0ed763e2b60416793a75cb16ec6c733
出典データセット
uspto-grants-2012_09
特許番号
US08273882B2

関連ノート

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