Water → HCID 178504841, compound

HRID 1158634Notes

Reaction equation

HRID 1158634 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.[CH3:26][S:27]([OH:29])=[O:28].[Na].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]([S:27]([CH3:26])(=[O:29])=[O:28])[N:11]=3)=[N:13][N:14]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1621282420277-69-4HCID 178515407HCID 178515407, compound

Product 1

HCID 178504841HCID 178504841, compoundYield 37.6%

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 (9 mg, 0.02 mmol) and sodium methanesulfinic acid (100 mg) in 1-methylpyrrolidin-2-one (2 mL) was heated at 150° C. for 3 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 preparative HPLC to give 7-[5-(4-fluorobenzyl)-4H-1,2,4-triazol-3-yl]-5-(methylsulfonyl)-1,6-naphthyridin-8-ol (3 mg, 33%) as a white solid. 1H NMR (CDCl3): δ 9.32 (d, J=8.4 Hz, 1 H), 9.25(d, J=4.4 Hz, 1 H), 7.75 (dd, J=8.4, 4.4 Hz, 1 H), 7.36 (dd, J=8.4, 5.6 Hz, 2 H), 7.03 (t, J=8.4 Hz, 2 H). 4.24 (s, 2 H), 3.42 (s, 3 H); MS m/z 400 (M+1).

Workup

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

Sources & evidence

ORD record
ord-7dc8caf090af4758bd3b029521767357
Source dataset
uspto-grants-2010_10
Patent number
US07812016B2

Reaction notes

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