1,2-Dichloroethane → HCID 66691716, compound

HRID 1808870Notes

Reaction equation

HRID 1808870 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:13]([C:14]([OH:16])=O)=[C:12]([CH3:17])[O:11][N:10]=1.[Cl:18][C:19]1[C:25]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:24][C:22]([NH2:23])=[C:21]([N+:32]([O-:34])=[O:33])[CH:20]=1.C(Cl)CCl.CN(C=O)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[NH2:23][C:22]1[C:21]([N+:32]([O-:34])=[O:33])=[CH:20][C:19]([Cl:18])=[C:25]([N:26]2[CH2:31][CH2:30][N:29]([C:14]([C:13]3[C:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[O:2][CH3:1])=[N:10][O:11][C:12]=3[CH3:17])=[O:16])[CH2:28][CH2:27]2)[CH:24]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 64841003-(2-Methoxyphenyl)-5-methyl-1,2-oxazole-4-carboxylic acidHCID 22273264HCID 22273264, compound

Product 1

HCID 66691716HCID 66691716, compoundYield 38.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3-(2-methoxyphenyl)-5-methylisoxazole-4-carboxylic acid (363 mg, 1.558 mmol, Preparation A), 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 N,N-dimethylpyridin-4-amine (571 mg, 4.67 mmol) in DCM (5 mL)/DMF (3 mL) was stirred overnight. The solution was diluted with DCM, then washed with water for three times. Purification via flash chromatography with 20% EtOAc in DCM provided the title compound (286 mg, 0.606 mmol, 38.9% yield). 1H-NMR (CDCl3, 400 MHz): δ8.11 (1H, s), 7.59 (1H, d, J=7.53 Hz), 7.47 (1H, t, J=8.53 Hz), 7.08 (1H, t, J=7.53 Hz), 6.99 (1H, d, J=7.28 Hz), 6.03 (1H, s), 3.80 (3H, s), 3.8 (2H, s) 3.22 (2H, s), 3.01 (2H, s), 2.57 (3H, s), 2.46 (2H, s).

Workup

  1. customprepared
  2. washwashed with water for three times
  3. customPurification via flash chromatography with 20% EtOAc in DCM

Sources & evidence

ORD record
ord-7365cab1201e497bba7f8b2e70a7516e
Source dataset
uspto-grants-2013_01
Patent number
US08362004B2

Reaction notes

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