Diisopropylethylamine → 1-Benzyl-2-oxo-1,2-dihydro-pyridine-4-carboxylic acid (7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-amide

HRID 1887854Notes

Reaction equation

HRID 1887854 reaction equation
[NH2:1][CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([Cl:14])=[CH:9][CH:10]=2)[N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:4]=1.[CH2:21]([N:28]1[CH:33]=[CH:32][C:31]([C:34](O)=[O:35])=[CH:30][C:29]1=[O:37])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Cl:14][C:8]1[CH:7]=[C:6]2[C:11]([C:12](=[O:13])[C:3]([CH2:2][NH:1][C:34]([C:31]3[CH:32]=[CH:33][N:28]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:29](=[O:37])[CH:30]=3)=[O:35])=[CH:4][N:5]2[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 181796161-Benzyl-2-oxo-1,2-dihydropyridine-4-carboxylic acidHCID 712083983-(aminomethyl)-7-chloro-1-phenylquinolin-4(1H)-one2×

Product 1

HCID 712173401-Benzyl-2-oxo-1,2-dihydro-pyridine-4-carboxylic acid (7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 20 mL round-bottomed flask, 3-(aminomethyl)-7-chloro-1-phenylquinolin-4(1H)-one (intermediate D) (50 mg, 0.176 mmol), 1-benzyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid (40.3 mg, 0.176 mmol), bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBrOP) (81.8 mg, 176 mmol) and N,N-diisopropylethylamine (0.092 mL, 0.527 mmol) were combined with CH2Cl2 (5.00 mL). The reaction mixture was stirred at room temperature, and the crude product was purified using preparative reverse-phase HPLC. MS calcd. for C29H23ClN3O3 [(M+H)+] 496.1, obsd. 496.0.

Workup

  1. customthe crude product was purified

Sources & evidence

ORD record
ord-bee211cb9fec45e38d7f1b578feb6e54
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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