Diisopropylethylamine → (E)-N-(2-(1-(3-(3,5-Dichlorophenyl)acryloyl)piperidin-4-yl)ethyl)-2-oxo-2,3-dihydrooxazole-5-carboxamide

HRID 1480426Notes

Reaction equation

HRID 1480426 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10](=[O:21])/[CH:11]=[CH:12]/[C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[CH:14]=2)[CH2:6][CH2:5]1.[O:22]=[C:23]1[NH:27][CH:26]=[C:25]([C:28](O)=[O:29])[O:24]1.CCN(C(C)C)C(C)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CN(C=O)C.CCOC(C)=O>[Cl:20][C:15]1[CH:14]=[C:13](/[CH:12]=[CH:11]/[C:10]([N:7]2[CH2:6][CH2:5][CH:4]([CH2:3][CH2:2][NH:1][C:28]([C:25]3[O:24][C:23](=[O:22])[NH:27][CH:26]=3)=[O:29])[CH2:9][CH2:8]2)=[O:21])[CH:18]=[C:17]([Cl:19])[CH:16]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 539814232-Hydroxy-1,3-oxazole-5-carboxylic acidHCID 86722654(E)-1-(4-(2-Aminoethyl)piperidin-1-yl)-3-(3,5-dichlorophenyl)prop-2-en-1-one

Product 1

HCID 86722657(E)-N-(2-(1-(3-(3,5-Dichlorophenyl)acryloyl)piperidin-4-yl)ethyl)-2-oxo-2,3-dihydrooxazole-5-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To (E)-1-(4-(2-aminoethyl)piperidin-1-yl)-3-(3,5-dichlorophenyl)prop-2-en-1-one (Example 30, step 4) (110 mg, 0.336 mmol) and 2-oxo-2,3-dihydrooxazole-5-carboxylic acid (Example 21, step 1) (167 mg, 0.504 mmol) in DMF (2 ml) was added DIPEA (0.470 mL, 2.69 mmol) and T3P® (50% in EtOAc, 1.571 ml, 2.69 mmol). The reaction mixture was stirred at RT overnight.

Sources & evidence

ORD record
ord-de5ba21e2c6543418c4acb86f3a978c5
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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