Triethylamine → 3'-Pyridin-4-ylethynyl-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-carboxylic acid (3,5-bis-trifluoromethylphenyl)amide

HRID 907572Notes

Reaction equation

HRID 907572 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[C:27](Cl)=[N:26][CH:25]=[CH:24][N:23]=3)[CH2:18][CH2:17]2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Cl.[C:32]([C:34]1[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=1)#[CH:33].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu]I>[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[C:27]([C:33]#[C:32][C:34]4[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=4)=[N:26][CH:25]=[CH:24][N:23]=3)[CH2:18][CH2:17]2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 162169314-Ethynylpyridine hydrochlorideHCID 59013946HCID 59013946, compound

Product 1

HCID 590139503'-Pyridin-4-ylethynyl-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-carboxylic acid (3,5-bis-trifluoromethylphenyl)amide

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
80 °C

Procedure

3′-Chloro-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid (3,5-bis-trifluoromethylphenyl)amide (200 mg, 0.441 mmol, prepared in Example 16b) was dissolved in 1.8 mL of acetonitrile. Another mixture was prepared containing 4-ethynylpyridine hydrochloride (125 mg, 0.896 mmol), palladium(II) acetate (12 mg, 0.053 mmol), copper(I) iodide (5 mg, 0.026 mmol), triphenylphosphine (28 mg, 0.107 mmol) and triethylamine (600 μL) in 600 μL of acetonitrile. The two mixtures were combined and stirred at 80° C. for 1 hr under a nitrogen atmosphere. The reaction mixture was filtered through Celite and concentrated under vacuum. The material was used without further purification.

Workup

  1. customAnother mixture was prepared
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationconcentrated under vacuum
  4. customThe material was used without further purification

Sources & evidence

ORD record
ord-3099bd554cd6430185b1ce20fb0a5570
Source dataset
uspto-grants-2011_09
Patent number
US08013156B2

Reaction notes

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