2-Bromopyridine → HCID 11328888, compound

HRID 1174728Notes

Reaction equation

HRID 1174728 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:17]([N+:18]([O-:20])=[O:19])=[C:16]([O:21][CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[N:15]=[CH:14][N:13]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Br[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1.C(N(CC)CC)C>CN(C=O)C>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:17]([N+:18]([O-:20])=[O:19])=[C:16]([O:21][CH:22]3[CH2:27][CH2:26][N:25]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=4)[CH2:24][CH2:23]3)[N:15]=[CH:14][N:13]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 79732-BromopyridineHCID 8471TriethylamineHCID 11257886(4-Methanesulfonyl-phenyl)-[5-nitro-6-(piperidin-4-yloxy)-pyrimidin-4-yl]-amine

Product 1

HCID 11328888HCID 11328888, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
165 °C

Procedure

Compound A2 (0.13 mmol, 50 mg), and 2-bromo-pyridine (0.53 mmol, 53 μL) were dissolved in DMF (1 mL) and triethylamine (0.46 mmol, 63 μL). The reaction was heated in a microwave at 165° C. for 40 minutes. The mixture was quenched with water and extracted with ethyl acetate. Removal of organic solvent in vacuo and purification by prep-TLC provided Compound A9 as a yellow solid (12 mg, 20%). 1H NMR (400 MHz, CDCl3) δ (ppm): 10.10 (s, 1H), 8.35 (s, 1H), 8.13 (m, 1H), 7.89 (d, 2H), 7.81 (d, 2H), 7.42 (m, 1H), 6.64 (d, 1H), 6.55 (m, 1H), 5.58 (heptet, 1H), 3.78 (m, 2H), 3.60 (m, 2H), 3.00 (s, 3H), 2.02 (m, 2H), 1.91 (m, 2H). LCMS (ESI), m/z 471.4 (M+H+, 100%).

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. customRemoval of organic solvent
  4. customin vacuo and purification by prep-TLC provided Compound A9 as a yellow solid (12 mg, 20%)

Sources & evidence

ORD record
ord-ca9045ebf4b94c278dd21b55f4e6345d
Source dataset
uspto-grants-2010_11
Patent number
US07838525B2

Reaction notes

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