Triethylamine → HCID 86702359, compound

HRID 1422567Notes

Reaction equation

HRID 1422567 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](/[CH:8]=[C:9]2/[C:10](=[O:15])[NH:11][C:12](=[O:14])[S:13]/2)[CH:5]=[CH:4][N:3]=1.[F:16][C:17]([F:28])([F:27])[C:18]1[CH:19]=[CH:20][C:21]([C:24](Cl)=[O:25])=[N:22][CH:23]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[O:14]=[C:12]1[NH:11][C:10](=[O:15])/[C:9](=[CH:8]/[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:24](=[O:25])[C:21]3[CH:20]=[CH:19][C:18]([C:17]([F:27])([F:16])[F:28])=[CH:23][N:22]=3)[N:7]=2)/[S:13]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 378596555-(Trifluoromethyl)pyridine-2-carbonyl chlorideHCID 86702356HCID 86702356, compound

Product 1

HCID 86702359HCID 86702359, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(Z)—N-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)pyrimidin-2-yl)-5-(trifluoromethyl)picolinamide was prepared as follows. A 2-dram vial was charged with (Z)-5-((2-aminopyrimidin-4-yl)methylene)thiazolidine-2,4-dione (22.2 mg, 0.100 mmol), Pyridine (1 mL), 5-(trifluoromethyl)picolinoyl chloride (63 mg, 0.301 mmol, 3 equiv.), triethylamine (60.7 mg, 0.599 mmol, 5.9 equiv.), and the reaction was shaken at RT. After 16 h, the reaction was treated with saturated sodium bicarbonate (3 mL) and extracted with DCE (3×3 mL). The combined organic layer was concentrated under reduced pressure and the residue was purified using reverse phase HPLC to provide the desired product (4 mg, 39.5 mg theoretical, 10%). LC-MS m/z 396.3 (M+1).

Workup

  1. extractionextracted with DCE (3×3 mL)
  2. concentrationThe combined organic layer was concentrated under reduced pressure
  3. customthe residue was purified

Sources & evidence

ORD record
ord-c228d88e7c214aa0b5243f8e97e2f2cd
Source dataset
uspto-grants-2015_01
Patent number
US08927525B2

Reaction notes

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