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

HRID 43060노트

반응식

HRID 43060 반응식
[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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-49643477164e488a82194f28a0ae18db
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536175B2

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