1,8-Diazabicyclo(5.4.0)undec-7-ene → Ethyl 3-{[1-(biphenyl-4-ylmethyl)-4,6-difluoro-5-iodo-1H-benzimidazol-2-yl]oxy}cyclopentanecarboxylate

HRID 340790노트

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HRID 340790 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.[OH:30][CH:31]1[CH2:35][CH2:34][CH:33]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:32]1.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:30][CH:31]2[CH2:35][CH2:34][CH:33]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:32]2)=[CH:3][CH:2]=1

참가 물질

7

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 53407781Ethyl 3-hydroxycyclopentanecarboxylate2회HCID 584825301-(biphenyl-4-ylmethyl)-4,6-difluoro-5-iodo-2-(methylsulfonyl)-1H-benzimidazole2회

생성물 1

HCID 67408440Ethyl 3-{[1-(biphenyl-4-ylmethyl)-4,6-difluoro-5-iodo-1H-benzimidazol-2-yl]oxy}cyclopentanecarboxylate

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, 0.650 g, 1.24 mmol) and ethyl 3-hydroxycyclopentanecarboxylate (Intermediate 9, 0.784 g, 4.96 mmol) in 4 mL of DMF was added DBU (0.747 mL, 4.96 mmol) dropwise via syringe. The reaction was heated overnight at 80° C., 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. Purification of the resulting residue by flash chromatography (3-25% EtOAc/hexanes) afforded the desired product. LCMS: calculated for C28H25F2IN2O3 602.41, observed m/e 602.9 (M+H)+ (Rt 2.57/4 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. customPurification of the resulting residue by flash chromatography (3-25% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-b6e2dd87be8243feaef17a5eac9bc664
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895596B2

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