Ethyl 2-({[5-(biphenyl-4-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}methyl)cyclopropanecarboxylate → 2-({[5-(biphenyl-4-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}methyl)cyclopropanecarboxylic acid

HRID 340801노트

반응식

HRID 340801 반응식
[C:1]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:25]([F:26])=[CH:24][C:10]3[NH:11][C:12]([O:14][CH2:15][CH:16]4[CH2:18][CH:17]4[C:19]([O:21]CC)=[O:20])=[N:13][C:9]=3[C:8]=2[F:27])=[CH:3][CH:2]=1.O([Si](C)(C)C)[K]>C1COCC1.CCOC(C)=O>[C:1]1([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:2]=[CH:3][C:4]([C:7]2[C:25]([F:26])=[CH:24][C:10]3[NH:11][C:12]([O:14][CH2:15][CH:16]4[CH2:18][CH:17]4[C:19]([OH:21])=[O:20])=[N:13][C:9]=3[C:8]=2[F:27])=[CH:5][CH:6]=1

참가 물질

5

반응물 2

HCID 67406772Ethyl 2-({[5-(biphenyl-4-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}methyl)cyclopropanecarboxylateHCID 178504318HCID 178504318, 화합물

생성물 1

HCID 533723792-({[5-(biphenyl-4-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}methyl)cyclopropanecarboxylic acid

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Ethyl 2-({[5-(biphenyl-4-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}methyl)cyclopropanecarboxylate (0.046 g, 0.102 mmol) was dissolved in 1 mL of THF and treated with KOTMS (0.037 g, 0.288 mmol). The reaction mixture was stirred at ambient temperature overnight, and then diluted with EtOAc and washed with 2 N HCl. The acidic aqueous layer was separated and further extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to give the title compound. LCMS: calculated for C24H18F2N2O3 420.41, observed m/e 420.9 (M+H)+ (Rt 2.21/4 min). 1H NMR (500 MHz, CD3OD): δ7.73-7.64 (m, 4H), 7.51 (d, 2H), 7.48-7.41 (m, 2H), 7.35 (m, 1H), 7.03 (d, 1H), 4.55 (dd, 1H), 4.29 (dd, 1H), 1.95 (m, 1H), 1.75 (m, 1H), 1.28 (m, 1H), 1.08 (m, 1H).

후처리

  1. washwashed with 2 N HCl
  2. customThe acidic aqueous layer was separated
  3. extractionfurther 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-009e28e3de9144418e89fb33742dedb0
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895596B2

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