Triethylamine → 7-Chloro-3-{[(6-morpholin-4-yl-pyridine-3-carbonyl)-amino]-methyl}-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid dimethylamide

HRID 1887842Notes

Reaction equation

HRID 1887842 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][N:8]=2)[CH2:3][CH2:2]1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C(N(CC)CC)C.[NH2:47][CH2:48][C:49]1[C:58](=[O:59])[C:57]2[C:52](=[CH:53][C:54]([Cl:60])=[CH:55][CH:56]=2)[N:51]([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[C:50]=1[C:67]([N:69]([CH3:71])[CH3:70])=[O:68]>CN(C=O)C>[CH3:70][N:69]([CH3:71])[C:67]([C:50]1[N:51]([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[C:52]2[C:57]([C:58](=[O:59])[C:49]=1[CH2:48][NH:47][C:11]([C:10]1[CH:9]=[N:8][C:7]([N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)=[CH:15][CH:14]=1)=[O:13])=[CH:56][CH:55]=[C:54]([Cl:60])[CH:53]=2)=[O:68]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733179PyBroPHCID 27764606-Morpholinonicotinic AcidHCID 712086753-(aminomethyl)-7-chloro-N,N-dimethyl-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxamide2×

Product 1

HCID 712081737-Chloro-3-{[(6-morpholin-4-yl-pyridine-3-carbonyl)-amino]-methyl}-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid dimethylamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Morpholinonicotinic acid (32.6 mg, 0.142 mmol), bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBrOP) (120 mg, 0.374 mmol) and triethylamine (100 mg, 0.137 mL, 0.988 mmol) were combined with DMF (4 mL). The reaction mixture was stirred at room temperature for 10 min. After this time, 3-(aminomethyl)-7-chloro-N,N-dimethyl-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxamide (intermediate C) (0.052 g, 0.156 mmol) was added. The reaction mixture was stirred at room temperature for 15 hr. The crude material was purified by flash chromatography (10% ethyl acetate-hexanes ramped to 100% ethyl acetate). MS calcd. for C29H28ClN5O4 [(M+H)+] 546.2, obsd. 546.0.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 15 hr
  2. customThe crude material was purified by flash chromatography (10% ethyl acetate-hexanes ramped to 100% ethyl acetate)

Sources & evidence

ORD record
ord-daf8e8c7d2854c769e78497cb220f24f
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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