3-Fluorobenzylamine → HCID 56847340, compound

HRID 242040Notes

Reaction equation

HRID 242040 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]([CH:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[C:4](=[O:22])[C:3]=1[C:23](O)=[O:24].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:59][C:60]1[CH:61]=[C:62]([CH:65]=[CH:66][CH:67]=1)[CH2:63][NH2:64]>C(Cl)Cl.O.CC(C)=O.CCCCCC>[F:59][C:60]1[CH:61]=[C:62]([CH2:63][NH:64][C:23]([C:3]2[C:4](=[O:22])[N:5]([CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[C:6]3[C:11]([C:2]=2[CH3:1])=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=3)=[O:24])[CH:65]=[CH:66][CH:67]=1

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 66584532HCID 66584532, compound

Product 1

HCID 56847340HCID 56847340, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 21880519Acetone hexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 280 mg (0.79 mmol) 4-methyl-2-oxo-1-(tetrahydro-2H-pyran-4-yl)-7-(trifluoromethyl)-1,2-dihydroquinoline-3-carboxylic acid in DCM (5 ml) were added 360 mg (0.95 mmol) HATU and 54 μl (3.15 mmol) DIPEA at 0° C. The reaction mixture was stirred for 5 min at 0° C. followed by the addition of 90 μl (0.79 mmol) 3-fluoro-benzylamine. The reaction mixture was stirred at RT for 4 h. Then the mixture was diluted with water (5 ml) and extracted with DCM (3×10 ml). The combined organic layers were washed with water (10 ml), brine (10 ml), dried over anhydrous Na2SO4 and concentrated in vacuum. After CC (acetone/hexane 1:3) of the residue, 210 mg (0.45 mmol, 57%) N-[(3-fluorophenyl)-methyl]-4-methyl-2-oxo-1-tetrahydro-pyran-4-yl-7-(trifluoromethyl)-1H-quinoline-3-carboxylic acid amide (example 44) were obtained. MS: m/z 463.2 [M+H]+.

Workup

  1. stirringThe reaction mixture was stirred at RT for 4 h
  2. extractionextracted with DCM (3×10 ml)
  3. washThe combined organic layers were washed with water (10 ml), brine (10 ml)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-1f7468e3ba8e4c68908f062e4fa731bc
Source dataset
uspto-grants-2014_02
Patent number
US08653102B2

Reaction notes

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