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

HRID 852295Notes

Reaction equation

HRID 852295 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-bd945bbc6a164293b65ec3ba37f2cf06
Source dataset
uspto-grants-2007_08
Patent number
US07253186B2

Reaction notes

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