p-Anisoyl chloride → N-(4-chloro-5-(4-(3-(2-methoxyphenyl)-5-methylisoxazole-4-carbonyl)piperazin-1-yl)-2-nitrophenyl)-4-methoxybenzamide

HRID 1808887Notes

Reaction equation

HRID 1808887 reaction equation
[NH2:1][C:2]1[C:3]([N+:31]([O-:33])=[O:32])=[CH:4][C:5]([Cl:30])=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[C:17]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][CH3:29])=[N:18][O:19][C:20]=3[CH3:21])=[O:15])[CH2:10][CH2:9]2)[CH:7]=1.[CH3:34][O:35][C:36]1[CH:44]=[CH:43][C:39]([C:40](Cl)=[O:41])=[CH:38][CH:37]=1.CCN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.N1CCCCC1>CN(C1C=CN=CC=1)C.ClCCCl>[Cl:30][C:5]1[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[C:17]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][CH3:29])=[N:18][O:19][C:20]=3[CH3:21])=[O:15])[CH2:10][CH2:9]2)=[CH:7][C:2]([NH:1][C:40](=[O:41])[C:39]2[CH:43]=[CH:44][C:36]([O:35][CH3:34])=[CH:37][CH:38]=2)=[C:3]([N+:31]([O-:33])=[O:32])[CH:4]=1

Participants

7

Reactant 4

HCID 7477p-Anisoyl chlorideHCID 8082PiperidineHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 66691716HCID 66691716, compound

Product 1

HCID 66693771N-(4-chloro-5-(4-(3-(2-methoxyphenyl)-5-methylisoxazole-4-carbonyl)piperazin-1-yl)-2-nitrophenyl)-4-methoxybenzamideYield 74.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (4-(5-amino-2-chloro-4-nitrophenyl)piperazin-1-yl)(3-(2-methoxyphenyl)-5-methylisoxazol-4-yl)methanone (16 mg, 0.034 mmol, Preparation L), 4-methoxybenzoyl chloride (12 mg, 0.068 mmol), DMAP (6 mg, 0.034 mmol), and BEMP (19 mg, 0.068 mmol) in DCE (1 mL) was heated at 80° C. for 3 h. Cooled down to RT, the mixture was treated with piperidine (0.3 ml) for 1 h and concentrated in vacuo. HPLC purification gave the title compound (15.7 mg, 0.025 mmol, 74.9% yield).

Workup

  1. temperatureCooled down to RT
  2. concentrationconcentrated in vacuo
  3. customHPLC purification

Sources & evidence

ORD record
ord-ae02d8f5d23f492d888d36442dc9081c
Source dataset
uspto-grants-2013_01
Patent number
US08362004B2

Reaction notes

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