Triethylamine → HCID 66583532, compound

HRID 242029Notes

Reaction equation

HRID 242029 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH2:6].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[CH3:41][C:42]1[C:51]2[C:46](=[CH:47][C:48]([C:52]([F:55])([F:54])[F:53])=[CH:49][CH:50]=2)[NH:45][C:44](=[O:56])[C:43]=1[C:57](O)=[O:58]>C1COCC1.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][NH:6][C:57]([C:43]2[C:44](=[O:56])[NH:45][C:46]3[C:51]([C:42]=2[CH3:41])=[CH:50][CH:49]=[C:48]([C:52]([F:54])([F:55])[F:53])[CH:47]=3)=[O:58])[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 668533-FluorobenzylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 665836552-Hydroxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid

Product 1

HCID 66583532HCID 66583532, compoundYield 83.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

926 mg (7.4 mmol) 3-Fluorobenzylamine, 2.55 g (6.7 mol) HATU and 2.7 ml (19.5 mmol) NEt3 were added to a solution of 1.82 g (6.7 mmol) 4-methyl-2-oxo-7-(trifluoromethyl)-1H-quinoline-3-carboxylic acid in THF (50 ml). The RS was stirred at 50° C. for 16 h and was then diluted with EtOAc (50 ml) at RT. The resulting precipitate was filtered off and dried in vacuo to give 2.10 g (5.6 mmol, 83%) N-[(3-Fluorophenyl)-methyl]-4-methyl-2-oxo-7-(trifluoromethyl)-1H-quinoline-3-carboxylic acid amide, which was used in the next step without further purification.

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. customdried in vacuo

Sources & evidence

ORD record
ord-8fd0b5d4d8fa4c7bbee52cb97b981429
Source dataset
uspto-grants-2014_02
Patent number
US08653102B2

Reaction notes

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