1,2-Dichloroethane → HCID 66695869, compound

HRID 1808873Notes

Reaction equation

HRID 1808873 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.[NH2:18][C:19]1[CH:26]=[C:25]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[C:24]([Cl:33])=[CH:23][C:20]=1[C:21]#[N:22].C(O)(C(F)(F)F)=O.C(Cl)CCl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[NH2:18][C:19]1[CH:26]=[C:25]([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)[C:24]([Cl:33])=[CH:23][C:20]=1[C:21]#[N:22]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6422Trifluoroacetic acidHCID 64841003-(2-Methoxyphenyl)-5-methyl-1,2-oxazole-4-carboxylic acidHCID 66692121HCID 66692121, compound

Product 1

HCID 66695869HCID 66695869, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The reaction mixture of 3-(2-methoxyphenyl)-5-methylisoxazole-4-carboxylic acid (10.00 mg, 0.043 mmol), 2-amino-5-chloro-4-(piperazin-1-yl)benzonitrile, 2 TFA (16.6 mg, 0.036 mmol), EDC (9.59 mg, 0.050 mmol) and DMAP (8.73 mg, 0.071 mmol) in DCM (1 mL) was stirred at room temperature overnight. The product was purified by preparative HPLC (0.1% TFA MeOH/H2O) to give 11 mg (52% yield) of the title compound. 1H-NMR (CDCl3, 400 MHz): δ 7.59 (1H, dd, J1=7.5 Hz, J2=1.8 Hz), 7.52-7.46 (1H, m), 7.33 (1H, s), 7.13-6.97 (2H, m), 6.06 (1H, s), 3.84 (2H, s), 3.80 (3H, s), 3.25 (2H, s), 2.98 (2H, s), 2.57 (3H, s), 2.43 (2H, s).

Workup

  1. customThe product was purified by preparative HPLC (0.1% TFA MeOH/H2O)

Sources & evidence

ORD record
ord-47db7d4e59c24a9c90814fd84e6b66ba
Source dataset
uspto-grants-2013_01
Patent number
US08362004B2

Reaction notes

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