1,2-Dichloroethane → HCID 66695754, compound

HRID 1808871Notes

Reaction equation

HRID 1808871 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[CH:25]=[C:24]([Cl:26])[C:23]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:22][C:20]=1[NH2:21].C(O)(C(F)(F)F)=O.C(Cl)CCl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[NH2:21][C:20]1[C:19]([Cl:18])=[CH:25][C:24]([Cl:26])=[C:23]([N:27]2[CH2:28][CH2:29][N:30]([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])[CH2:31][CH2:32]2)[CH:22]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6422Trifluoroacetic acidHCID 64841003-(2-Methoxyphenyl)-5-methyl-1,2-oxazole-4-carboxylic acidHCID 66692368HCID 66692368, compound

Product 1

HCID 66695754HCID 66695754, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The reaction mixture of 3-(2-methoxyphenyl)-5-methylisoxazole-4-carboxylic acid (0.131 g, 0.561 mmol), 2,4-dichloro-5-(piperazin-1-yl)aniline, 2 TFA (0.253 g, 0.534 mmol), EDC (0.123 g, 0.641 mmol) and DMAP (0.130 g, 1.07 mmol) in DCM (4 mL) was stirred at RT overnight. The crude product was purified by flash chromatography (MeOH/DCM, gradient 2%-4%, Rf 0.31 with 3% MeOH) to give 0.221 g of the title compound (90% yield). 1H-NMR (CD3OD, 400 MHz): δ 7.57-7.50 (2H, m), 7.19 (1H, s), 7.18-7.07 (2H, m), 6.43 (1H, s), 3.81 (3H, s), 3.74 (2H, s), 3.24 (2H, s), 2.88 (2H, s), 2.53 (3H, s), 2.35 (2H, s).

Workup

  1. customThe crude product was purified by flash chromatography (MeOH/DCM, gradient 2%-4%, Rf 0.31 with 3% MeOH)

Sources & evidence

ORD record
ord-1e1e2fdf6d3542818a78b0caf40c776e
Source dataset
uspto-grants-2013_01
Patent number
US08362004B2

Reaction notes

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