Trifluoroacetic acid → 4-Cyano-1H-imidazole-2-carboxylic acid [4-(1-azido-1-methyl-ethyl)-2-cyclohex-1-enyl-phenyl]-amide

HRID 1508019노트

반응식

HRID 1508019 반응식
[C:1]1([C:7]2[CH:12]=[C:11]([C:13](O)([CH3:15])[CH3:14])[CH:10]=[CH:9][C:8]=2[NH:17][C:18]([C:20]2[NH:21][CH:22]=[C:23]([C:25]#[N:26])[N:24]=2)=[O:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[N-:27]=[N+:28]=[N-:29].[Na+].C(O)(C(F)(F)F)=O.CCOC(C)=O>C(Cl)(Cl)Cl>[N:27]([C:13]([C:11]1[CH:10]=[CH:9][C:8]([NH:17][C:18]([C:20]2[NH:21][CH:22]=[C:23]([C:25]#[N:26])[N:24]=2)=[O:19])=[C:7]([C:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=2)[CH:12]=1)([CH3:15])[CH3:14])=[N+:28]=[N-:29]

참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 178458516HCID 178458516, 화합물

생성물 1

HCID 1784580634-Cyano-1H-imidazole-2-carboxylic acid [4-(1-azido-1-methyl-ethyl)-2-cyclohex-1-enyl-phenyl]-amide수율 84.6%

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
0 °C

실험 절차

To a mixture of 4-cyano-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(1-hydroxy-1-methyl-ethyl)-phenyl]-amide (as prepared in example 1, step (h), 15.0 mg, 0.0428 mmol) and NaN3 (27.8 mg, 0.428 mmol) in 1 mL of chloroform at 0° C. under Ar was added TFA (49 μL, 0.64 mmol). The resulting mixture was stirred at 0° C. for 1 h under Ar. Treated with 30 mL of EtOAc, the mixture was washed with saturated aqueous NaHCO3 (10 mL), brine (10 mL) and dried (Na2SO4). Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (0-5% EtOAc/DCM) gave 13.6 mg (84%) of the title compound as a white solid. Mass spectrum (ESI, m/z): Calcd. for C20H21N7O, 376.2 (M+H). found 376.0.

후처리

  1. washthe mixture was washed with saturated aqueous NaHCO3 (10 mL), brine (10 mL)
  2. dry with materialdried (Na2SO4)
  3. customRemoval of the solvent under reduced pressure

출처 및 근거

ORD 기록
ord-201901924f3b4aaa826a3f2816090966
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221797B2

반응 노트

불러오는 중…