4-[3-(2-Fluorophenyl)-[1,2,3]triazolo[1,5-a]quinazolin-5-yl]piperazine-1-carboxylic acid tert-butyl ester → 3-(2-Fluorophenyl)-5-(piperazin-1-yl)-[1,2,3]triazolo[1,5-a]quinazoline

HRID 1581635Notes

Reaction equation

HRID 1581635 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]3[N:24]=[N:25][C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[F:33])=[C:16]3[N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>ClCCl>[F:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:26]1[N:25]=[N:24][N:17]2[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[N:15][C:16]=12

Participants

3

Reactant 1

HCID 700311884-[3-(2-Fluorophenyl)-[1,2,3]triazolo[1,5-a]quinazolin-5-yl]piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 700325103-(2-Fluorophenyl)-5-(piperazin-1-yl)-[1,2,3]triazolo[1,5-a]quinazolineYield 109.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[3-(2-Fluorophenyl)-[1,2,3]triazolo[1,5-α]quinazolin-5-yl]piperazine-1-carboxylic acid tert-butyl ester (0.28 g, 0.63 mmol) was dissolved in dichloromethane (5 ml) and hydrogen chloride bubbled through the reaction (2×10 min). The precipitate was filtered and washed with diethyl ether to give 3-(2-fluorophenyl)-5-(piperazin-1-yl)-[1,2,3]triazolo[1,5-α]quinazoline as a white solid (0.24 g, 100%). HCl salt: δH (360 MHz; DMSO) 3.30-3.41 (4H, m), 3.79-3.83 (4H, m), 7.35-7.41 (2H, m), 7.44-7.51 (1H, m), 7.78 (1H, ddd, J=8, 8 and 1), 8.05-8.12 (2H, m), 8.27 (1H, d, J=8), 8.62 (1H, dd, J=8 and 1); m/z (ES+) 349 (M+H+).

Workup

  1. customhydrogen chloride bubbled through the reaction (2×10 min)
  2. filtrationThe precipitate was filtered
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-47ee02e20dbd438b9e88f252f64a5ed2
Source dataset
uspto-grants-2004_05
Patent number
US06730681B2

Reaction notes

Loading…