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

반응식

HRID 1992034 반응식
[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]

참가 물질

6

반응물 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

생성물 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 ester수율 88.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0dd15a61265e4a0b867955eba5cd0180
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07645755B2

연결된 노트

불러오는 중…