Water → HCID 178516736, compound

HRID 1158636Notes

Reaction equation

HRID 1158636 reaction equation
Br[C:2]1[N:11]=[C:10]([C:12]2[NH:16][C:15]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[N:14][N:13]=2)[C:9]([OH:25])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[NH:26]1[CH2:31][CH2:30][NH:29][CH2:28][C:27]1=[O:32].O>CN1CCCC1=O>[F:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][C:15]2[NH:16][C:12]([C:10]3[C:9]([OH:25])=[C:8]4[C:3]([CH:4]=[CH:5][CH:6]=[N:7]4)=[C:2]([N:29]4[CH2:30][CH2:31][NH:26][C:27](=[O:32])[CH2:28]4)[N:11]=3)=[N:13][N:14]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 231360Piperazin-2-oneHCID 178515407HCID 178515407, compound

Product 1

HCID 178516736HCID 178516736, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 5-bromo-7-[5-(4-fluorobenzyl)-4H-1,2,4-triazol-3-yl)-1,6-naphthyridin-8-ol (10 mg, 0.03 mmol) and piperazin-2-one (60 mg, 0.60 mmol) in 1-methylpyrrolidin-2-one (2 mL) was heated at 150° C. for 18 hours. The resultant solution was cooled to room temperature and water was added. The solids which formed were removed by filtration and further purified by prep HPLC to give 4-{7-[5-(4-Fluorobenzyl)-4H-1,2,4-triazol-3-yl]-8-hydroxy-1,6-naphthyridin-5-yl}piperazin-2-one (7 mg, 67%) as a white solid. 1H NMR (CD3OD/CDCl3): δ 9.03 (d, J=4.4 Hz, 1 H), 8.48 (d, J=8.4 Hz, 1 H), 7.64 (dd, J=8.4, 4.4 Hz, 1 H), 7.32 (dd, J=8.4, 5.6Hz, 2 H), 6.97 (t, J=8.4Hz, 2 H). 4.13 (s, 2 H), 4.10 (5,2 H), 3.60 (m, 2 H), 3.42 (m, 2 H); 19F NMR (CD3OD/CDCl3): δ −117.93; MS m/z 420 (M+1).

Workup

  1. customThe solids which formed
  2. customwere removed by filtration
  3. customfurther purified by prep HPLC

Sources & evidence

ORD record
ord-f60e1bf737904aff993d221dddeb6102
Source dataset
uspto-grants-2010_10
Patent number
US07812016B2

Reaction notes

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