Diisopropylethylamine → HCID 58994553、化合物

HRID 1508029ノート

反応式

HRID 1508029 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 58994553HCID 58994553、化合物収率 91%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b79f339bebe94bee8ce7d3c38b63b116
出典データセット
uspto-grants-2015_12
特許番号
US09221797B2

反応ノート

読み込み中…