Imidazole → HCID 67176053, 화합물

HRID 238412노트

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HRID 238412 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:9]2[C:20]2[CH:25]=[CH:24][C:23]([C:26](=[O:28])[NH2:27])=[CH:22][C:21]=2[CH3:29])=[CH:4][CH:3]=1.[NH:30]1[CH:34]=[CH:33][N:32]=[CH:31]1.N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I>[N:30]1([C:2]2[CH:7]=[CH:6][C:5]([N:8]3[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:9]3[C:20]3[CH:25]=[CH:24][C:23]([C:26](=[O:28])[NH2:27])=[CH:22][C:21]=3[CH3:29])=[CH:4][CH:3]=2)[CH:34]=[CH:33][N:32]=[CH:31]1

참가 물질

7

반응물 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 58297378HCID 58297378, 화합물

생성물 1

HCID 67176053HCID 67176053, 화합물수율 51%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 679Dimethyl Sulfoxide용매

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온도
130 °C

실험 절차

A mixture of ethyl 3-(1-(4-bromophenyl)-2-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-3-yl)propanoate (50 mg, 0.11 mmol), imidazole (68 mg, 10 mmol), L-proline (13 mg, 0.11 mmol), CuI (42 mg, 0.22 mmol), K2CO3 (76 mg, 0.55 mmol) and 4 Å molecular sieve (100 mg) in DMSO (3 mL) was heated at 130° C. for 24 h. After being cooled down to room temperature, the reaction mixture was filtered, and the filter cake was washed with ethyl acetate (10 mL×3). The combined filtrate was washed with saturated NaHCO3 aqueous solution (30 mL), and the aqueous layer was extracted with ethyl acetate (15 mL×3). The combined organic layers were washed with brine, dried over MgSO4, and concentrated. The residue was purified by preparative TLC (eluting with 7% methanol in dichloromethane) to give ethyl 3-(1-(4-(1H-imidazol-1-yl)phenyl)-2-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-3-yl)propanoate, (5-3, R1=1H-imidazol-1-yl) (25 mg, yield: 51%), which was used in the next step without further purification.

후처리

  1. temperatureAfter being cooled down to room temperature
  2. filtrationthe reaction mixture was filtered
  3. washthe filter cake was washed with ethyl acetate (10 mL×3)
  4. washThe combined filtrate was washed with saturated NaHCO3 aqueous solution (30 mL)
  5. extractionthe aqueous layer was extracted with ethyl acetate (15 mL×3)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe residue was purified by preparative TLC (eluting with 7% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-0365bbf407c34f0cbff72cb634791124
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642628B2

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