Hydrochloric Acid → 4-Bromobenzoic acid 2-(3,5-dichlorophenyl)-1,3-dioxo-tetrahydro-pyrazolo[1,2-alpha][1,2,4]triazol-6-yl Ester

HRID 1838463Notes

Reaction equation

HRID 1838463 reaction equation
CCN=C=NCCCN(C)C.Cl.[Cl:13][C:14]1[CH:15]=[C:16]([N:21]2[C:25](=[O:26])[N:24]3[CH2:27][CH:28]([OH:30])[CH2:29][N:23]3[C:22]2=[O:31])[CH:17]=[C:18]([Cl:20])[CH:19]=1.[Br:32][C:33]1[CH:41]=[CH:40][C:36]([C:37](O)=[O:38])=[CH:35][CH:34]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:20][C:18]1[CH:17]=[C:16]([N:21]2[C:22](=[O:31])[N:23]3[CH2:29][CH:28]([O:30][C:37](=[O:38])[C:36]4[CH:40]=[CH:41][C:33]([Br:32])=[CH:34][CH:35]=4)[CH2:27][N:24]3[C:25]2=[O:26])[CH:15]=[C:14]([Cl:13])[CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 114644-Bromobenzoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 121120082-(3,5-Dichlorophenyl)-6-hydroxy-dihydro-pyrazolo[1,2-alpha][1,2,4]triazole-1,3-dione

Product 1

HCID 102777864-Bromobenzoic acid 2-(3,5-dichlorophenyl)-1,3-dioxo-tetrahydro-pyrazolo[1,2-alpha][1,2,4]triazol-6-yl EsterYield 12.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

EDCI, HCl (70 mg, 0.37 mmol) and DMAP (4 mg, 0.03 mmol) were added to a solution of 2-(3,5-dichlorophenyl)-6-hydroxy-dihydro-pyrazolo[1,2-α][1,2,4]triazole-1,3-dione (100 mg, 0.33 mmol) (Preparation 6), TEA (92 μl, 0.66 mmol) and 4-bromobenzoic acid (73 mg, 0.36 mmol) in DCM (2 ml). After 72 h at RT, the reaction mixture was washed with a citric acid solution (0.5 M) and a sodium bicarbonate solution, then concentrated. The residue was purified with preparative HPLC to yield the above compound (20 mg). 1H NMR (CDCl3):7.71 (2H, d, J=7 Hz), 7.55 (2H, d, J=7 Hz), 7.40 (3H, m), 5.67 (1H, m), 4.34 (2H, d, J=12.7 Hz), 3.80 (2H, dd, J1=12.7 Hz, J2=2.8 Hz).

Workup

  1. washthe reaction mixture was washed with a citric acid solution (0.5 M)
  2. concentrationa sodium bicarbonate solution, then concentrated
  3. customThe residue was purified with preparative HPLC

Sources & evidence

ORD record
ord-69173ee3d88a44e1a78fc42af4fce7a1
Source dataset
uspto-grants-2004_01
Patent number
US06673825B2

Reaction notes

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