Triethylamine → HCID 11225078, compound

HRID 1174731Notes

Reaction equation

HRID 1174731 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[CH2:29][CH2:30][O:31][CH2:32][CH3:33].C(N(CC)CC)C>CN(C=O)C>[CH2:30]([O:31][CH2:32][CH2:33][N:25]1[CH2:26][CH2:27][CH:22]([O:21][C:16]2[N:15]=[CH:14][N:13]=[C:12]([NH:11][C:8]3[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)[C:17]=2[N+:18]([O-:20])=[O:19])[CH2:23][CH2:24]1)[CH3:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 611412-Bromoethyl ethyl etherHCID 11257886(4-Methanesulfonyl-phenyl)-[5-nitro-6-(piperidin-4-yloxy)-pyrimidin-4-yl]-amine

Product 1

HCID 11225078HCID 11225078, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Compound A2 (0.13 mmol, 50 mg), and 1-bromo-2-ethoxy-ethane (0.65 mmol, 99 mg) were dissolved in DMF (1 mL) and triethylamine (0.91 mmol, 127 μL). The reaction was heated in a microwave at 80° C. for 20 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 A12 as a yellow solid (20 mg, 33%). 1H NMR (400 MHz, CDCl3) δ (ppm): 10.06 (s, 1H), 8.29 (s, 1H), 7.84 (d, 2H), 7.74 (d, 2H), 5.39 (s broad, 1H), 3.53 (m, 2H), 3.39 (q, 2H), 2.86 (s, 3H), 2.77 (m, 2H), 2.65 (m, 3H), 2.04 (m, 2H), 1.92 (m, 3H), 1.09 (m, 3H). LCMS (ESI), m/z 466.3 (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 A12 as a yellow solid (20 mg, 33%)

Sources & evidence

ORD record
ord-1e5f5c0b557646c299d2d9052e272e29
Source dataset
uspto-grants-2010_11
Patent number
US07838525B2

Reaction notes

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