Acetic Acid → 3-(2-((2H-1,2,3-Triazol-4-yl)amino)-5-chlorobenzyl)cyclobutanecarboxylic acid

HRID 1519142

반응식

HRID 1519142 반응식
C([N:8]1[C:12]([NH:13][C:14]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:15]=2[CH:16]=[C:17]2[CH2:20][CH:19]([C:21]([OH:23])=[O:22])[CH2:18]2)=[CH:11][N:10]=[N:9]1)C1C=CC=CC=1.C(O)(=O)C>CCOC(C)=O.CO.Br[Zn]Br.[Pd]>[N:10]1[NH:9][N:8]=[C:12]([NH:13][C:14]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:15]=2[CH2:16][CH:17]2[CH2:20][CH:19]([C:21]([OH:23])=[O:22])[CH2:18]2)[CH:11]=1

참가 물질

7

반응물 2

HCID 176Acetic Acid2회HCID 867240613-(2-((1-benzyl-1H-1,2,3-triazol-5-yl)amino)-5-chlorobenzylidene)cyclobutanecarboxylic acid

생성물 1

HCID 752029263-(2-((2H-1,2,3-Triazol-4-yl)amino)-5-chlorobenzyl)cyclobutanecarboxylic acid수율 3.9%

시약·촉매·용매 4

HCID 23938Palladium촉매HCID 24375Zinc bromide (ZnBr2); Zinc Dibromide촉매HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 3-(2-((1-benzyl-1H-1,2,3-triazol-5-yl)amino)-5-chlorobenzylidene)cyclobutanecarboxylic acid 7 g (75 mg, 0.19 mmol) and dibromozinc (17.1 mg, 0.076 mmol) in EtOAc (2 mL) and MeOH (2 mL) was added 10% Pd on C [wet Degussa type] (40 mg, 0.038 mmol). The reaction was then flushed with hydrogen via vacuum/hydrogen cycles (3×) and the mixture stirred under a hydrogen atmosphere for 2 h at room temperature. Additional 10% Pd on C [wet Degussa type] (40 mg, 0.038 mmol) was added and stirred under hydrogen for a further 1 h. Acetic acid (23 mg, 21.60 μL, 0.38 mmol) was then added and mixture stirred under hydrogen overnight. Additional acetic acid (22 mg, 21.60 μL, 0.38 mmol) was added and stirred under hydrogen atmosphere again overnight. The reaction mixture was then filtered through celite washing through with methanol. The filtrate was concentrated and the material purified by FractionLynx to afford the title compound I-28 as a white solid (1.5 TFA salt) (4.0 mg, 3.9% yield). 1H NMR (500 MHz, d6-DMSO) δ 7.78 (1H, brs), 7.59 (1H, brs), 7.46 (1H, brs), 7.10-7.12 (1H, m), 7.06 (1H, d), 2.87-2.94 (1H, m), 2.72 (2H, d), 2.50-2.55 (1H, masked signal), 2.18-2.25 (2H, m), 1.84-1.90 (2H, m). MS m/z: 307.1 (M+H)+.

후처리

  1. customThe reaction was then flushed with hydrogen via vacuum/hydrogen cycles (3×)
  2. additionAdditional 10% Pd on C [wet Degussa type] (40 mg, 0.038 mmol) was added
  3. stirringstirred under hydrogen for a further 1 h
  4. stirringmixture stirred under hydrogen overnight
  5. stirringstirred under hydrogen atmosphere again overnight
  6. filtrationThe reaction mixture was then filtered through celite
  7. washwashing through with methanol
  8. concentrationThe filtrate was concentrated
  9. customthe material purified by FractionLynx

출처 및 근거

ORD 기록
ord-0d87f2c1ae944850834697c7746a734e
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073875B2

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