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

HRID 1711232노트

반응식

HRID 1711232 반응식
[C:1]1([C:7]2[CH:12]=[C:11]([C:13]([OH:16])([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.OS(O)(=O)=O.CO.[C:34]([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]1([C:7]2[CH:12]=[C:11]([C:13]([O:16][CH3:34])([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

참가 물질

6

반응물 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 178458516HCID 178458516, 화합물

생성물 1

HCID 1784948834-Cyano-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(1-methoxy-1-methyl-ethyl)-phenyl]-amide수율 44%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-cyano-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(1-hydroxy-1-methyl-ethyl)-phenyl]-amide (as prepared in example 12, 18.0 mg, 0.0514 mmol) in 1 mL of DCM was added conc H2SO4 (50 μL) followed by 50 μL of MeOH. The resulting mixture was stirred at RT for 0.5 h and then treated with 10 mL of saturated NaHCO3 aqueous solution. The mixture was extracted with EtOAc (2×20 mL). The combined organic layers were washed with H2O (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 (1% MeOH/DCM) gave 8.2 mg (44%) of the title compound as a white solid. 1H-NMR (CDCl3; 400 MHz): δ 12.31 (s, 1H), 9.65 (s, 1H), 8.30 (d, 1H, J=8.6 Hz), 7.76 (s, 1H), 7.35 (dd, 1H, J=8.6, 2.3 Hz), 7.25 (d, 1H, J=2.3 Hz), 5.88 (m, 1H), 3.11 (s, 3H), 2.23-2.37 (m, 4H), 1.75-1.90 (m, 4H), 1.55 (s, 6H).

후처리

  1. extractionThe mixture was extracted with EtOAc (2×20 mL)
  2. washThe combined organic layers were washed with H2O (10 mL), brine (10 mL)
  3. dry with materialdried (Na2SO4)
  4. customRemoval of the solvent under reduced pressure

출처 및 근거

ORD 기록
ord-56ef6c5f59744b33b02ecb0759048e51
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790724B2

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