Diisopropylethylamine → HCID 58994553, 화합물

HRID 1508029노트

반응식

HRID 1508029 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([NH2:12])=[O:11])=[CH:4][C:3]=1[C:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=1.[C:19]([C:21]1[N:22]=[C:23]([C:34]([O-])=[O:35])[N:24]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[CH:25]=1)#[N:20].[K+].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[C:10]([CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:34]([C:23]2[N:24]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[CH:25]=[C:21]([C:19]#[N:20])[N:22]=2)=[O:35])=[C:3]([C:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=2)[CH:4]=1)(=[O:11])[NH2:12]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 58994428HCID 58994428, 화합물HCID 67188357potassium 4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylate

생성물 1

HCID 58994553HCID 58994553, 화합물수율 91%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 3-(4-amino-3-cyclohex-1-enyl-phenyl)-propionamide (as prepared in the previous step, 85.0 mg, 0.378 mmol), potassium 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylate (as prepared in Example 1, step (d), 117 mg, 0.383 mmol) and PyBroP (179 mg, 0.383 mmol) in 2.5 mL of DMF was added DIEA (182 μL, 1.04 mmol). After stirring at RT for 16 h, the mixture was treated with 30 mL of EtOAc and washed with H2O (2×10 mL), brine (10 mL) and dried (Na2SO4). The organic solvent was evaporated in vacuo and the residue was purified by flash chromatography on silica gel (0-2% MeOH/DCM) to give 156 mg (91%) of the title compound as a white solid. Mass spectrum (ESI, m/z): Calcd. for C26H35N5O3Si, 494.3 (M+H). found 494.0.

후처리

  1. washwashed with H2O (2×10 mL), brine (10 mL)
  2. dry with materialdried (Na2SO4)
  3. customThe organic solvent was evaporated in vacuo
  4. customthe residue was purified by flash chromatography on silica gel (0-2% MeOH/DCM)

출처 및 근거

ORD 기록
ord-b79f339bebe94bee8ce7d3c38b63b116
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221797B2

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