3-Pyridinylboronic acid → HCID 67502008, compound

HRID 513309Notes

Reaction equation

HRID 513309 reaction equation
[F:1][C:2]1[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:3]=1[CH2:4][NH:5][C:6]1[C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=[C:8]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[CH:7]=1.[N:33]1[CH:38]=[CH:37][CH:36]=[C:35](B(O)O)[CH:34]=1>C(Cl)Cl.N1C=CC=CC=1.CO.CC([O-])=O.CC([O-])=O.[Cu+2]>[F:1][C:2]1[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:3]=1[CH2:4][NH:5][C:6]1[C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=[C:8]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([CH:22]3[CH2:23][CH2:24][N:25]([C:35]4[CH:34]=[N:33][CH:38]=[CH:37][CH:36]=4)[CH2:26][CH2:27]3)=[CH:20][CH:21]=2)[CH:7]=1

Participants

7

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 675004384-(2,3-Difluorobenzylamino)-6-(4-(piperidin-4-yl)phenylamino)nicotinamide

Product 1

HCID 67502008HCID 67502008, compound

Reagents, catalysts & solvents 4

HCID 8895Cupric acetateCatalystHCID 887MethanolSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

The mixture of 4-(2,3-difluorobenzylamino)-6-(4-(piperidin-4-yl)phenylamino)nicotinamide (Example 209) (100 mg, 0.21 mmol), 3-pyridineboronic acid (265 mg, 2.10 mmol), Cu(OAc)2 powder (190 mg, 1.05 mmol) in 5 mL DCM and 1 mL pyridine was stirred at RT for 2 days. It was diluted with methanol and filtered through celite. The filtrate was treated with TFA and concentrated in vacuo. The residue was subjected to reverse phase HPLC to isolate the title compound. MS found for C29H28F2N6O as (M+H)+ 515.5. UV: λ=268 nm. 1H NMR: (CD3OD) δ 8.41 (1H, m), 8.16 (1H, s), 8.09 (1H, s), 8.06 (1H, s), 7.81 (1H, m), 7.35 (2H, dt, J=8.4; 2.0 Hz), 7.24 (1H, m), 7.16 (1H, m), 7.12-7.07 (3H, m), 5.79 (1H, s), 4.55 (2H, s), 4.12 (2H, m), 3.13 (2H, m), 2.91 (1H, m), 2.04 (2H, m), 1.87 (2H, m) ppm.

Workup

  1. filtrationfiltered through celite
  2. additionThe filtrate was treated with TFA
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-369733ed42884049bbef3658374b03ac
Source dataset
uspto-grants-2015_08
Patent number
US09102625B2

Reaction notes

Loading…