1,2-Dichloroethane → (4-(5-Amino-2-chloro-4-nitrophenyl)piperazin-1-yl)(5-methyl-3-(naphthalen-1-yl)isoxazol-4-yl)methanone

HRID 1808889Notes

Reaction equation

HRID 1808889 reaction equation
[C:1]1([C:11]2[C:15]([C:16](O)=[O:17])=[C:14]([CH3:19])[O:13][N:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl:20][C:21]1[C:27]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[CH:26][C:24]([NH2:25])=[C:23]([N+:34]([O-:36])=[O:35])[CH:22]=1.C(Cl)CCl.CN(C=O)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[NH2:25][C:24]1[C:23]([N+:34]([O-:36])=[O:35])=[CH:22][C:21]([Cl:20])=[C:27]([N:28]2[CH2:33][CH2:32][N:31]([C:16]([C:15]3[C:11]([C:1]4[C:10]5[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=5)[CH:4]=[CH:3][CH:2]=4)=[N:12][O:13][C:14]=3[CH3:19])=[O:17])[CH2:30][CH2:29]2)[CH:26]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 22273264HCID 22273264, compoundHCID 641580523-(1-Naphthyl)-5-methylisoxazole-4-carboxylic acid

Product 1

HCID 68032125(4-(5-Amino-2-chloro-4-nitrophenyl)piperazin-1-yl)(5-methyl-3-(naphthalen-1-yl)isoxazol-4-yl)methanone

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(1-naphthyl)-5-methylisoxazole-4-carboxylic acid (394 mg, 1.558 mmol), 4-chloro-2-nitro-5-(piperazin-1-yl)aniline (400 mg, 1.558 mmol, prepared as described in [El-Abadelah, M. M.; Nazer, M. Z.; El-Abadla, N. S.; Awadallah, A. M. Asian Journal of Chemistry 1999, 11(4), 1463-1468.]), EDC (448 mg, 2.337 mmol), and DMAP (571 mg, 4.67 mmol) in DCM (5 mL)/DMF (3 mL) was stirred overnight.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-d8cad55c004542258ecb6e0f672997c2
Source dataset
uspto-grants-2013_01
Patent number
US08362004B2

Reaction notes

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