Trifluoroacetic acid → 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-[(2-methylpiperazin-1-yl)methyl]-3,4-dihydroquinazolin-2(1H)-one

HRID 394099Notes

Reaction equation

HRID 394099 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([CH2:18][N:19]2[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH:20]2[CH3:32])[CH:15]=[C:14]2[C:9]=1[CH2:10][NH:11][C:12](=[O:41])[N:13]2[C:33]1[C:38]([Cl:39])=[CH:37][CH:36]=[CH:35][C:34]=1[Cl:40].FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([CH2:18][N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH:20]2[CH3:32])[CH:15]=[C:14]2[C:9]=1[CH2:10][NH:11][C:12](=[O:41])[N:13]2[C:33]1[C:34]([Cl:40])=[CH:35][CH:36]=[CH:37][C:38]=1[Cl:39]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22648157Tert-butyl 4-{[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]methyl}-3-methylpiperazine-1-carboxylate

Product 1

HCID 101647505-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-[(2-methylpiperazin-1-yl)methyl]-3,4-dihydroquinazolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-{[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]methyl}-3-methylpiperazine-1-carboxylate (186 mg, 0.30 mmol) in methylene chloride (1 mL) at 0° C. was added trifluoroacetic acid (0.92 mL) dropwise. Then the reaction was stirred at rt for 1 h. Removal of the solvent and subsequent purification by preparative thin layer chromatography using 8% of 2N ammonium in methanol/methylene chloride as eluent provided the 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-[(2-methylpiperazin-1-yl)methyl]-3,4-dihydroquinazolin-2(1H)-one compound. 1H NMR (CDCl3, 500 MHz): δ 0.98 (m, 3H), 2.06 (m, 2H), 2.32 (s, 1H), 2.48 (m, 1H), 2.63 (m, 1H), 2.72 (t, 1H, J=10.2 Hz), 2.84 (m, 2H), 3.15 (dd, 1H, J1=14.0 Hz, J2=6.0 Hz), 3.86 (t, 1H, J=13.2 Hz), 4.34 (abq, 2H, J=14.2 Hz), 5.23 (s, 1H), 6.15 (d, 1H, J=9.4 Hz), 6.88 (s, 1H), 7.20-7.60 (m, 7H). MS (API-ES+): 517 (M+H).

Workup

  1. customRemoval of the solvent and subsequent purification by preparative thin layer chromatography

Sources & evidence

ORD record
ord-bc1a2006f36e477b84d680bbbcefc90f
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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