N-bromobutanimide → HCID 57935934, compound

HRID 2035394Notes

Reaction equation

HRID 2035394 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]([N+]([O-])=O)=[CH:8][CH:9]=2)[N:4]=1)C.BrN1C(=O)CCC1=O.[CH3:34][N:35]1[CH2:41][CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1>C(Cl)(Cl)(Cl)Cl.O1CCCC1.[Pd].[C]>[CH2:20]([O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[N:12]1[C:11](=[O:22])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[C:3]1[CH2:1][N:38]1[CH2:39][CH2:40][CH2:41][N:35]([CH3:34])[CH2:36][CH2:37]1)[CH3:21]

Participants

7

Reactant 3

HCID 67184N-bromobutanimideHCID 2283491-MethylhomopiperazineHCID 58228565HCID 58228565, compound

Product 1

HCID 57935934HCID 57935934, compound

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 5943Carbon TetrachlorideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Briefly, 2-amino-4-nitrobenzoic acid was acylated with propionyl chloride in triethylamine (TEA) and tetrahydrofuran (THF). The acylated compound was refluxed with 2-ethoxyaniline in phosphorus oxychloride (POCl3) and toluene to produce 2-ethyl-7-nitro-3-(2-ethoxyphenyl)quinazolin-4(3H)-one. The 2-ethyl-7-nitro-3-(2-ethoxyphenyl)quinazolin-4(3H)-one was brominated with N-bromosuccinimide (NBS) in carbon tetrachloride, the product of which was subsequently reacted with N-methylhomopiperazine in THF. The product of this reaction was subjected to hydrogenation conditions using catalytic amounts of Pd/carbon (10% Pd) to afford Compound 10.

Sources & evidence

ORD record
ord-b802e5063cb34944b94b1fa810388a94
Source dataset
uspto-grants-2013_11
Patent number
US08575143B2

Reaction notes

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