Triethylamine → HCID 60197496, compound

HRID 878033Notes

Reaction equation

HRID 878033 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[NH:14][CH3:15])=[CH:6][C:5]([F:16])=[CH:4][N:3]=1.CCN(CC)CC.[F:24][C:25]([F:40])([F:39])[C:26]1[CH:27]=[C:28]([CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1)[C:29](Cl)=[O:30]>C(Cl)Cl>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:14]([CH3:15])[C:29](=[O:30])[C:28]2[CH:27]=[C:26]([C:25]([F:40])([F:39])[F:24])[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=2)=[CH:6][C:5]([F:16])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 86670704HCID 86670704, compound

Product 1

HCID 60197496HCID 60197496, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of (2-chloro-5-fluoro-[3,4′]bipyridinyl-3′-yl)-methyl-amine (80 mg, 0.34 mmol) in CH2Cl2 (10 mL) were added Et3N (0.187 mL, 1.35 mmol) and 3,5-bis(trifluoromethyl)-benzoyl chloride (0.061 mL, 0.34 mmol, CAS RN 1271-19-8) at 25° C. and the resulting reaction mixture was stirred for 4 hours at 25° C. The mixture was diluted with CH2Cl2 (20 mL), the organic layer was washed with saturated aqueous NaHCO3 solution (2×20 mL) and brine (25 mL), dried over Na2SO4, filtered and concentrated under vacuum to afford the crude product which was purified using preparative HPLC. Off-white solid (22 mg, 14%). MS (ESI): m/z=478.4 [M+H]+.

Workup

  1. customthe resulting reaction mixture
  2. washthe organic layer was washed with saturated aqueous NaHCO3 solution (2×20 mL) and brine (25 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e0eaab487a70450685301e1820f45047
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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