Triethylamine → HCID 178429293, compound

HRID 242120Notes

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.[OH:41][C:42]1[C:51]([C:52](O)=[O:53])=[C:50]([CH3:55])[C:49]2[C:44](=[CH:45][C:46]([C:56]([F:59])([F:58])[F:57])=[CH:47][CH:48]=2)[N:43]=1>C1COCC1.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH:6][C:52]([C:51]1[C:42]([OH:41])=[N:43][C:44]2[C:49]([C:50]=1[CH3:55])=[CH:48][CH:47]=[C:46]([C:56]([F:58])([F:59])[F:57])[CH:45]=2)=[O:53]

Participants

Conditions

Temperature: 50 °C

Procedure

508 mg (4.1 mmol) 3-fluorobenzylamine, 1.4 g (3.7 mmol) HATU and 1.5 ml (10.7 mmol) NEt3 were added consecutively to a solution of 1.0 g (3.7 mmol) 2-hydroxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid (synthesis see Example 4 Section a)) in THF (28 ml) and the solution was then stirred for 16 h at 50° C. The solution was subsequently diluted with EtOAc (30 ml). The resultant precipitate was filtered off and suspended in a EtOAc/MeOH/DCM mixture. Concentration in a vacuum was subsequently carried out. 1.0 g (2.6 mmol, 71%) N-(3-fluorobenzyl)-2-hydroxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid amide was obtained as a residue. The raw product was further converted without additional purification.

Workup

customsynthesis
filtrationThe resultant precipitate was filtered off
concentrationConcentration in a vacuum

Sources & evidence

ORD record: ord-c4a61f7331f84fbcab979a141091ced8
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653101B2

Reaction notes

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