1,4-Dioxane hydrochloride → HCID 23077599, compound

HRID 1349506Notes

Reaction equation

HRID 1349506 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:37])[C:11]([NH:29]C(=O)OC(C)(C)C)=[CH:12][N:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[C:22]([Cl:27])[CH:21]=3)[C:15](=[O:28])[C:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O1CCOCC1>O1CCOCC1>[NH2:29][C:11]1[C:10](=[O:37])[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:14]2[C:15](=[O:28])[N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[C:22]([Cl:27])[CH:21]=3)[CH2:17][CH2:18][N:13]2[CH:12]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 58859192HCID 58859192, compound

Product 1

HCID 23077599HCID 23077599, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl [9-benzyloxy-2-(3-chloro-4-fluorobenzyl)-1,8-dioxo-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrazin-7-yl]carbamate (179 mg) in dioxane (2 ml) was added 4N hydrochloric acid/dioxane solution (2 ml) and the mixture was stirred at room temperature for 3.5 hr. The solvent was evaporated and aqueous sodium hydrogen carbonate solution was added to the obtained residue. The mixture was extracted with chloroform. The chloroform layer was dried, concentrated and purified by silica gel column chromatography (ethyl acetate:methanol=5:1) to give 7-amino-9-benzyloxy-2-(3-chloro-4-fluorobenzyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione (88 mg).

Workup

  1. customThe solvent was evaporated
  2. additionaqueous sodium hydrogen carbonate solution was added to the obtained residue
  3. extractionThe mixture was extracted with chloroform
  4. dry with materialThe chloroform layer was dried
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (ethyl acetate:methanol=5:1)

Sources & evidence

ORD record
ord-15ed96f7cf0845e4930f09d17b8f951e
Source dataset
uspto-grants-2007_05
Patent number
US07211572B2

Reaction notes

Loading…