Diisopropylcarbodiimide → 2'-Fluoro-3-methyl-N-[5-(2-pyrazinyl)-2-pyridinyl][2,4'-bipyridine]-5-acetamide

HRID 1036270Notes

Reaction equation

HRID 1036270 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH2:15][C:16]([OH:18])=O)=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1.[N:19]1[CH:24]=[CH:23][N:22]=[CH:21][C:20]=1[C:25]1[CH:26]=[CH:27][C:28]([NH2:31])=[N:29][CH:30]=1.C(N=C=NC(C)C)(C)C>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH2:15][C:16]([NH:31][C:28]3[CH:27]=[CH:26][C:25]([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][N:19]=4)=[CH:30][N:29]=3)=[O:18])=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 584476922-(2'-Fluoro-3-methyl-2,4'-bipyridin-5-yl)acetic acidHCID 592592255-(Pyrazin-2-yl)pyridin-2-amine

Product 1

HCID 469273642'-Fluoro-3-methyl-N-[5-(2-pyrazinyl)-2-pyridinyl][2,4'-bipyridine]-5-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the mixture of 2-(2′-fluoro-3-methyl-2,4′-bipyridin-5-yl)acetic acid 193-2 (50 mg, 0.2 mmol) and 5-(pyrazin-2-yl)pyridin-2-amine 86-3 (36 mg, 0.2 mmol) in DCM (1 mL) was added N,N′-Diisopropylcarbodiimide (46 μL, 0.3 mmol) at room temperature. The mixture was stirred at room temperature for 24 hours. The solvent was removed by rotary evaporation and the residue was dissolved in DMSO and then purified by reverse-phase HPLC to give 2-(2′-fluoro-3-methyl-2,4′-bipyridin-5-yl)-N-(5-(pyrazin-2-yl)pyridin-2-yl)acetamide 199 as white solid. MS m/z 401.2 (M+1); 1H NMR 400 MHz (DMSO-d6) δ11.07 (s, 1H), 9.25 (d, 1H, J=1.6 Hz), 9.05 (m, 1H), 8.66 (m, 1H), 8.57 (d, 1H, J=2.4 Hz), 8.47-8.45 (m, 2H), 8.28 (d, 1H, J=5.2 Hz), 8.16 (d, 1H, J=8.8 Hz), 7.71 (d, 1H, J=1.6 Hz), 7.51-7.49 (m, 1H), 7.31 (s, 1H), 3.82 (s, 2H), 2.31 (s, 3H).

Workup

  1. customThe solvent was removed by rotary evaporation
  2. dissolutionthe residue was dissolved in DMSO
  3. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-d1503119ed0045c282e0fec775257ab5
Source dataset
uspto-grants-2013_10
Patent number
US08546396B2

Reaction notes

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