Water → HCID 86645341, compound

HRID 1260700Notes

Reaction equation

HRID 1260700 reaction equation
[Cl:1][C:2]1[C:11]([C:12](Cl)=[O:13])=[C:10]([CH3:15])[C:9]2[C:4](=[CH:5][C:6]([C:16]([F:19])([F:18])[F:17])=[CH:7][CH:8]=2)[N:3]=1.[F:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][NH2:25].CCN(C(C)C)C(C)C.O>O1CCOCC1.CCOC(C)=O>[Cl:1][C:2]1[C:11]([C:12]([NH:25][CH2:24][C:23]2[CH:26]=[CH:27][CH:28]=[C:21]([F:20])[CH:22]=2)=[O:13])=[C:10]([CH3:15])[C:9]2[C:4](=[CH:5][C:6]([C:16]([F:19])([F:18])[F:17])=[CH:7][CH:8]=2)[N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 668533-FluorobenzylamineHCID 81531DiisopropylethylamineHCID 86645342HCID 86645342, compound

Product 1

HCID 86645341HCID 86645341, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 15.6 g (50.6 mmol) 2-chloro-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid chloride in 1,4-dioxane (85 ml) was added in drops to a solution of 7.6 g (60.8 mmol) 3-fluorobenzylamine and 10.3 ml (60.8 mmol) DIPEA in 1,4-dioxane (87 ml). The RS was subsequently stirred for 60 min at RT. Dilution was then carried out with water and EtOAc. The organic phase was separated, washed with a 4N aq. NH4Cl sol. and brine, dried over MgSO4 and concentrated in a vacuum. 19.4 g (48.9 mmol, 97%) 2-chloro-N-(3-fluorobenzyl)-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid amide was obtained as a residue. The raw product was further converted without additional purification.

Workup

  1. customThe organic phase was separated
  2. washwashed with a 4N aq. NH4Cl sol. and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in a vacuum

Sources & evidence

ORD record
ord-24e2dd8a6a404c449efecefe7c3f77d9
Source dataset
uspto-grants-2013_06
Patent number
US08470852B2

Reaction notes

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