Piperazine → HCID 58228556, compound

HRID 2035392Notes

Reaction equation

HRID 2035392 reaction equation
[CH2:1]([C:3]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH2:20][CH3:21])[C:11](=[O:22])[C:10]2[C:5](=[CH:6][C:7]([Cl:23])=[CH:8][CH:9]=2)[N:4]=1)[CH3:2].BrN1C(=O)CCC1=O.[NH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.[Cl:38][C:39]1[CH:49]=[CH:48][C:42]([O:43][CH2:44][C:45](Cl)=[O:46])=[CH:41][CH:40]=1>C(Cl)(Cl)(Cl)Cl.O1CCCC1.C(N(CC)CC)C>[Cl:38][C:39]1[CH:49]=[CH:48][C:42]([O:43][CH2:44][C:45]([N:32]2[CH2:37][CH2:36][N:35]([CH:1]([C:3]3[N:12]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[O:19][CH2:20][CH3:21])[C:11](=[O:22])[C:10]4[C:5](=[CH:6][C:7]([Cl:23])=[CH:8][CH:9]=4)[N:4]=3)[CH3:2])[CH2:34][CH2:33]2)=[O:46])=[CH:41][CH:40]=1

Participants

8

Reactant 4

HCID 4837PiperazineHCID 67184N-bromobutanimideHCID 77771p-Chlorophenoxyacetyl chlorideHCID 58228561HCID 58228561, compound

Product 1

HCID 58228556HCID 58228556, compound

Reagents, catalysts & solvents 3

HCID 5943Carbon TetrachlorideSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

Briefly, 2-amino-4-chlorobenzoic acid was acylated with propionyl chloride in triethylamine (TEA) and tetrahydrofuran (THF). The acylated compound was refluxed with 2-ethoxyaniline in phosphorus trichloride and toluene to produce 2-ethyl-7-chloro-3-(2-ethoxyphenyl)quinazolin-4(3H)-one. The 2-ethyl-7-chloro-3-(2-ethoxyphenyl)quinazolin-4(3H)-one was brominated with N-bromosuccinimide (NBS) in carbon tetrachloride, the product of which was subsequently reacted with piperazine in THF. The piperazinyl moiety was acylated with 4-chlorophenoxyacetyl chloride in THF and TEA to yield the final product.

Sources & evidence

ORD record
ord-447fcaaa3e354c588790c82c819fc01a
Source dataset
uspto-grants-2013_11
Patent number
US08575143B2

Reaction notes

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