1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 67409526, 화합물

HRID 340798

반응식

HRID 340798 반응식
[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:12]3[CH:13]=[C:14]([F:19])[C:15]([I:18])=[C:16]([F:17])[C:11]=3[N:10]=[C:9]2S(C)(=O)=O)=[CH:3][CH:2]=1.[CH2:30]([O:32][C:33]([CH:35]1[CH2:37][CH:36]1[CH2:38][OH:39])=[O:34])[CH3:31].C1CCN2C(=NCCC2)CC1>CN(C=O)C.CCOC(C)=O.O>[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:12]3[CH:13]=[C:14]([F:19])[C:15]([I:18])=[C:16]([F:17])[C:11]=3[N:10]=[C:9]2[O:39][CH2:38][CH:36]2[CH2:37][CH:35]2[C:33]([O:32][CH2:30][CH3:31])=[O:34])=[CH:3][CH:2]=1

참가 물질

7

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 13005707Ethyl 2-(hydroxymethyl)cyclopropanecarboxylate2회HCID 584825301-(biphenyl-4-ylmethyl)-4,6-difluoro-5-iodo-2-(methylsulfonyl)-1H-benzimidazole2회

생성물 1

HCID 67409526HCID 67409526, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

To a solution of 1-(biphenyl-4-ylmethyl)-4,6-difluoro-5-iodo-2-(methylsulfonyl)-1H-benzimidazole (Intermediate 5, 0.500 g, 0.954 mmol) and 2-hydroxymethyl-cyclopropanecarboxylic acid ethyl ester (Intermediate 10, 0.550 g, 3.81 mmol) in 3.2 mL of DMF was added DBU (0.575 mL, 3.81 mmol) dropwise via syringe. The reaction was heated at 80° C. for 2 h, and then diluted with EtOAc and H2O. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated. The resulting crude residue was purified on silica gel (eluted 2-15% then 15-20% EtOAc/hexanes: gradient elution) to furnish the desired product. LCMS: calculated for C27H23F2IN2O3 588.38, observed m/e 588.9 (M+H)+ (Rt 2.51/4 min).

후처리

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting crude residue was purified on silica gel (
  8. washeluted 2-15%
  9. wash15-20% EtOAc/hexanes: gradient elution)

출처 및 근거

ORD 기록
ord-6dd66103cc324a6ca8cdde952822eeb7
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895596B2

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