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

HRID 1887831Notes

Reaction equation

HRID 1887831 reaction equation
[CH2:1]([N:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:16])=O)=[CH:10][C:9]1=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C(N(CC)C(C)C)(C)C.[NH2:51][CH2:52][C:53]1[C:62](=[O:63])[C:61]2[C:56](=[CH:57][C:58]([Cl:64])=[CH:59][CH:60]=2)[N:55]([C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)[C:54]=1[C:71]1[O:72][CH:73]=[CH:74][N:75]=1>CN(C=O)C>[Cl:64][C:58]1[CH:57]=[C:56]2[C:61]([C:62](=[O:63])[C:53]([CH2:52][NH:51][C:14]([C:11]3[CH:12]=[CH:13][N:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[C:9](=[O:17])[CH:10]=3)=[O:16])=[C:54]([C:71]3[O:72][CH:73]=[CH:74][N:75]=3)[N:55]2[C:65]2[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=2)=[CH:60][CH:59]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 181796161-Benzyl-2-oxo-1,2-dihydropyridine-4-carboxylic acidHCID 712083323-aminomethyl-7-chloro-2-oxazol-2-yl-1-phenyl-1H-quinolin-4-one2×

Product 1

HCID 712173291-Benzyl-2-oxo-1,2-dihydro-pyridine-4-carboxylic acid (7-chloro-2-oxazol-2-yl-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 10 mL round-bottomed flask, 1-benzyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid (32.6 mg, 0.142 mmol), bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBrOP) (66.3 mg, 0.142 mmol) and N,N-diisopropylethylamine (73.5 mg, 0.099 mL, 0.569 mmol) were combined with DMF (2 mL). The reaction mixture was stirred at room temperature for 10 min. After this time, 3-aminomethyl-7-chloro-2-oxazol-2-yl-1-phenyl-1H-quinolin-4-one (intermediate A) was added (0.050 g, 0.142 mmol). The reaction mixture was stirred at room temperature for 3 hr. The product was purified using flash chromatography (40% ethyl acetate/hexane ramped to 100% ethyl acetate/hexanes). MS calcd. for C32H24ClN4O4 [(M+H)+] 563.1, obsd. 563.3.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 hr
  2. customThe product was purified

Sources & evidence

ORD record
ord-8a717c4bc36a4e079b40f4554f59b3c0
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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