2-Methoxy-6-(tributylstannyl)pyrazine → 6-(6-methoxypyrazin-2-yl)-8-(4-morpholinophenylamino)-2,7-naphthyridin-1(2H)-one

HRID 1034946Notes

Reaction equation

HRID 1034946 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[CH:15][CH:14]=3)[N:11]=1)[C:8](=[O:25])[NH:7][CH:6]=[CH:5]2.[CH3:26][O:27][C:28]1[CH:33]=[N:32][CH:31]=[C:30]([Sn](CCCC)(CCCC)CCCC)[N:29]=1>CN(C=O)C>[CH3:26][O:27][C:28]1[N:29]=[C:30]([C:2]2[CH:3]=[C:4]3[C:9](=[C:10]([NH:12][C:13]4[CH:18]=[CH:17][C:16]([N:19]5[CH2:24][CH2:23][O:22][CH2:21][CH2:20]5)=[CH:15][CH:14]=4)[N:11]=2)[C:8](=[O:25])[NH:7][CH:6]=[CH:5]3)[CH:31]=[N:32][CH:33]=1

Participants

4

Reactant 2

HCID 164271032-Methoxy-6-(tributylstannyl)pyrazineHCID 866495446-chloro-8-(4-morpholinophenylamino)-2,7-naphthyridin-1(2H)-one

Product 1

HCID 580941186-(6-methoxypyrazin-2-yl)-8-(4-morpholinophenylamino)-2,7-naphthyridin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-chloro-8-(4-morpholinophenylamino)-2,7-naphthyridin-1(2H)-one (30 mg, 0.084 mmol) was dissolved in DMF (1 mL) in a microwave vial and 2-methoxy-6-(tributylstannyl)pyrazine (40 mg, 0.1 mmol) was added followed by PdCl2dppf (6.1 mg, 0.0084 mmol) at room temperature. The vial was flushed with nitrogen and closed the cap and subjected to microwave irradiation at 135 C for 60 minutes. The reaction mixture was diluted with DMSO and purified by prep HPLC. The compound was isolated as a TFA salt. 1H NMR (400 MHz, DMSO-d6) δ 11.14 (s, 1H), 8.96 (s, 1H), 8.33 (s, 1H), 7.68 (s, 1H), 7.67 (d, 2H, J=8.8 Hz), 7.38 (m, 1H), 6.95 (d, 2H, J=8.8 Hz), 6.57 (d, 1H, J=7.2 Hz), 4.0 (s, 3H), 3.69 (t, 4H, J=4.8 Hz), 3.04 (t, 4H, J=4.8 Hz); MS m/z 431.2 (M+1).

Workup

  1. additionwas added
  2. customThe vial was flushed with nitrogen
  3. customclosed the
  4. customcap
  5. customirradiation at 135 C for 60 minutes
  6. additionThe reaction mixture was diluted with DMSO
  7. custompurified by prep HPLC

Sources & evidence

ORD record
ord-12bbe4ab827b4a8a904d18d2a773b3d3
Source dataset
uspto-grants-2013_10
Patent number
US08546370B2

Reaction notes

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