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

HRID 2409603

반응식

HRID 2409603 반응식
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]

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3499dd225b254d5e9b3f395482acde41
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815901B2

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