Chlorotrimethylsilane → 2-[4-(4H-1,2,4-triazol-4-yl)phenyl]acetic acid

HRID 1453791ノート

反応式

HRID 1453791 の反応式
[CH:1]([NH:3][NH:4][CH:5]=O)=O.C[Si](Cl)(C)C.CCN(CC)CC.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]([OH:29])=[O:28])=[CH:22][CH:21]=1>N1C=CC=CC=1>[N:4]1[N:3]=[CH:1][N:19]([C:20]2[CH:21]=[CH:22][C:23]([CH2:26][C:27]([OH:29])=[O:28])=[CH:24][CH:25]=2)[CH:5]=1

参加物

6

反応物 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 123421,2-HydrazinedicarboxaldehydeHCID 145334-Aminophenylacetic acid

生成物 1

HCID 204742832-[4-(4H-1,2,4-triazol-4-yl)phenyl]acetic acid収率 93%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
100 °C

実験手順

Adapting a protocol by Catarzi et al (J. Med. Chem., 2001, 44, 3157-3165), diformylhydrazine (352 mg, 4.0 mmol) and then dropwise trimethylsilyl chloride (2.53 mL, 20 mmol) and Et3N (1.30 mL, 9.3 mmol) were added to a suspension of 4-aminophenylacetic acid (201 mg, 1.33 mmol) in anhydrous pyridine. The mixture was heated at 100° C. overnight, volatiles were removed at reduced pressure and the resulting solid was treated with water (6 mL), collected, washed with H2O and dried in vacuo to provide 251 mg (93%) of 141JP01 as a light brown solid. LCMS m/z 204[M+H]+. 1H-NMR (DMSO-d6) δ 9.05 (s, 2H), 7.62 (d, 1H, J=8.6), 7.40 (d, 1H, J=8.2), 3.61 (s, 2H).

後処理

  1. customvolatiles were removed at reduced pressure
  2. additionthe resulting solid was treated with water (6 mL)
  3. customcollected
  4. washwashed with H2O
  5. customdried in vacuo

出典と根拠

ORDレコード
ord-95f550f9158f46e6a4088ee52ac3c84a
出典データセット
uspto-grants-2009_01
特許番号
US07476682B2

反応ノート

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