Ethyl 3-{[5-(biphenyl-4-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclopentanecarboxylate → 3-{[5-(biphenyl-4-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclo-pentanecarboxylic acid

HRID 340793노트

반응식

HRID 340793 반응식
[C:1]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:26]([F:27])=[CH:25][C:10]3[NH:11][C:12]([O:14][CH:15]4[CH2:19][CH2:18][CH:17]([C:20]([O:22]CC)=[O:21])[CH2:16]4)=[N:13][C:9]=3[C:8]=2[F:28])=[CH:3][CH:2]=1.O([Si](C)(C)C)[K]>C1COCC1.CCOC(C)=O>[C:1]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:2]=[CH:3][C:4]([C:7]2[C:26]([F:27])=[CH:25][C:10]3[NH:11][C:12]([O:14][CH:15]4[CH2:19][CH2:18][CH:17]([C:20]([OH:22])=[O:21])[CH2:16]4)=[N:13][C:9]=3[C:8]=2[F:28])=[CH:5][CH:6]=1

참가 물질

5

반응물 2

HCID 67406155Ethyl 3-{[5-(biphenyl-4-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclopentanecarboxylateHCID 178504318HCID 178504318, 화합물

생성물 1

HCID 533723783-{[5-(biphenyl-4-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclo-pentanecarboxylic acid

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Ethyl 3-{[5-(biphenyl-4-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclopentanecarboxylate (0.039 g, 0.084 mmol) was dissolved in 1 mL of THF and treated with KOTMS (0.032 g, 0.253 mmol). The reaction mixture was stirred overnight at ambient temperature, and then diluted with EtOAc and washed with 2 N HCl. The layers were separated and the aqueous layer was further extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to afford the title compound as a white solid. LCMS: calculated for C25H20F2N2O3 434.43, observed m/e 434.9 (M+H)+ (Rt 2.24/4 min). 1H NMR (500 MHz, d6-DMSO): δ7.77 (d, 2H), 7.73 (d, 2H), 7.56-7.46 (m, 4H), 7.39 (m, 111), 7.14 (d, 1H), 5.50 (m, 1H), 2.95 (m, 1H), 2.20-1.80 (m, 6H).

후처리

  1. washwashed with 2 N HCl
  2. customThe layers were separated
  3. extractionthe aqueous layer was further extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-be5e999678c0489b993412ddfd601f19
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895596B2

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