Diisopropylethylamine → HCID 58994553、化合物

HRID 1190094ノート

反応式

HRID 1190094 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-7102626ec7cf446eb255cd9751785cd2
出典データセット
uspto-grants-2014_03
特許番号
US08674100B2

反応ノート

読み込み中…