Ethyl Acetate → HCID 178424523, 화합물

HRID 1190098노트

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HRID 1190098 반응식
[C:1]([CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]2[N:16](COCC[Si](C)(C)C)[CH:17]=[C:18]([C:20]#[N:21])[N:19]=2)=[O:14])=[C:8]([C:30]2[CH2:35][CH2:34][C:33]([CH3:37])([CH3:36])[CH2:32][CH:31]=2)[CH:7]=1)(=[O:3])[NH2:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O>C1COCC1>[C:1]([CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]2[NH:16][CH:17]=[C:18]([C:20]#[N:21])[N:19]=2)=[O:14])=[C:8]([C:30]2[CH2:35][CH2:34][C:33]([CH3:37])([CH3:36])[CH2:32][CH:31]=2)[CH:7]=1)(=[O:3])[NH2:2]

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 58994394HCID 58994394, 화합물

생성물 1

HCID 178424523HCID 178424523, 화합물수율 24%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-(2-carbamoyl-ethyl)-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide (as prepared in the previous step, 160 mg, 0.307 mmol) and tetrabutylammonium fluoride (357 μL, 0.357 mmol, 1.0 M in THF) in 4.5 mL of THF was stirred at reflux for 1.5 h under Ar. After cooling to RT, the mixture was treated with EtOAc (40 mL), washed with saturated aq NaHCO3 (5 mL), brine (10 mL) and dried (Na2SO4). The organic layer was concentrated in vacuo and the residue was purified by flash chromatography on silica gel (5% MeOH/DCM) to give 29.2 mg (24%) of the title compound as a white solid. 1H-NMR (CD3OD; 400 MHz): δ 8.09 (d, 1H, J=8.3 Hz), 7.98 (s, 1H), 7.14 (dd, 1H, J=8.3, 2.1 Hz), 7.07 (d, 1H, J=2.1 Hz), 5.71 (m, 1H), 2.89 (t, 2H, J=7.7 Hz), 2.50 (t, 2H, J=7.7 Hz), 2.29 (m, 2H), 2.06 (m, 2H), 1.57 (t, 2H, J=6.3 Hz), 1.07 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C22H25N5O2, 392.2 (M+H). found 392.2.

후처리

  1. temperatureat reflux for 1.5 h under Ar
  2. washwashed with saturated aq NaHCO3 (5 mL), brine (10 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationThe organic layer was concentrated in vacuo
  5. customthe residue was purified by flash chromatography on silica gel (5% MeOH/DCM)

출처 및 근거

ORD 기록
ord-02e8c937b26d4bdcaafecd969d589bfe
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674100B2

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