Diisopropylethylamine → 4(4-{[4-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbonyl]-amino}-3-cyclohept-1-enyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1992034

反応式

HRID 1992034 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([C:21]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH:22]=3)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[K+].[C:29]([C:31]1[N:32]=[C:33]([C:44]([O-])=[O:45])[N:34]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])[CH:35]=1)#[N:30].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:44]([C:33]3[N:34]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])[CH:35]=[C:31]([C:29]#[N:30])[N:32]=3)=[O:45])=[C:16]([C:21]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH:22]=3)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 586945894-(4-Amino-3-cyclohept-1-enyl-phenyl)-piperidine-1-carboxylic acid tert-butyl esterHCID 67188357potassium 4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylate

生成物 1

HCID 586945874(4-{[4-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbonyl]-amino}-3-cyclohept-1-enyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester収率 88.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 108 mg (0.292 mmol) 4-(4-amino-3-cyclohept-1-enyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (as prepared in the previous step) in 10 mL CH2Cl2 was treated with 97.9 mg (0.321 mmol) 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylate potassium salt (as prepared in Example 1, step (d)), 204 mg (0.437 mmol) PyBrOP, and 152 μL (0.874 mmol) DIEA and stirred at RT for 17 h. The mixture was diluted with CH2Cl2 (20 mL) and washed with saturated NaHCO3 (1×15 mL) and water (1×15 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. Silica gel chromatography of the residue on a Varian MegaBond Elut 50-gm column with 10-25% EtOAc-hexane afforded 160 mg (88%) of the title compound as an off-white solid: Mass spectrum (ESI, m/z): Calcd. for C30H42N5O4Si, 563.3 (M−C4H9+2H), found 563.9.

後処理

  1. washwashed with saturated NaHCO3 (1×15 mL) and water (1×15 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-0dd15a61265e4a0b867955eba5cd0180
出典データセット
uspto-grants-2010_01
特許番号
US07645755B2

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