3-Fluorobenzylamine → HCID 56847142, compound

HRID 242031Notes

Reaction equation

HRID 242031 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[F:34][C:35]1[CH:36]=[C:37]([CH:40]=[CH:41][CH:42]=1)[CH2:38][NH2:39].[CH2:43]([N:47]1[C:56]2[C:51](=[CH:52][CH:53]=[C:54]([C:57]([F:60])([F:59])[F:58])[CH:55]=2)[C:50]([CH3:61])=[C:49]([C:62](O)=[O:63])[C:48]1=[O:65])[CH2:44][CH2:45][CH3:46]>CN(C=O)C.O.CCOC(C)=O.CCCCCC>[CH2:43]([N:47]1[C:56]2[C:51](=[CH:52][CH:53]=[C:54]([C:57]([F:60])([F:59])[F:58])[CH:55]=2)[C:50]([CH3:61])=[C:49]([C:62]([NH:39][CH2:38][C:37]2[CH:40]=[CH:41][CH:42]=[C:35]([F:34])[CH:36]=2)=[O:63])[C:48]1=[O:65])[CH2:44][CH2:45][CH3:46]

Participants

8

Reactant 4

HCID 668533-FluorobenzylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66584630HCID 66584630, compound

Product 1

HCID 56847142HCID 56847142, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

349 mg (0.9 mmol) HATU, 550 μl (3.1 mmol) DIPEA and 90 μl (0.8 mmol) 3-fluoro-benzylamine were added to a solution of 250 mg (0.8 mmol) 1-butyl-4-methyl-2-oxo-7-(trifluoromethyl)-1H-quinoline-3-carboxylic acid in DMF (3 ml) at RT and stirring was continued for 3 h. The RS was then diluted with water (20 ml) and extracted with EtOAc (3×30 ml). The combined organic layers were washed with water and brine, dried over Na2SO4 and concentrated in vacuo. After CC (EtOAc/hexane 1:4) of the residue, 180 mg (0.4 mmol, 54%) 1-butyl-N-[(3-fluorophenyl)-methyl]-4-methyl-2-oxo-7-(trifluoromethyl)-1H-quinoline-3-carboxylic acid amide (example 2) was obtained. MS: m/z 435.2 [M+H]+.

Workup

  1. extractionextracted with EtOAc (3×30 ml)
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c403d9d5fd364dfd98ba046593a29eec
Source dataset
uspto-grants-2014_02
Patent number
US08653102B2

Reaction notes

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