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

HRID 1519142ノート

反応式

HRID 1519142 の反応式
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

参加物

7

反応物 2

HCID 176Acetic Acid2 回HCID 867240613-(2-((1-benzyl-1H-1,2,3-triazol-5-yl)amino)-5-chlorobenzylidene)cyclobutanecarboxylic acid

生成物 1

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

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 24375Zinc bromide (ZnBr2); Zinc Dibromide触媒HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-0d87f2c1ae944850834697c7746a734e
出典データセット
uspto-grants-2015_07
特許番号
US09073875B2

反応ノート

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