Sodium Sulfate → HCID 178516866, compound

HRID 1943216Notes

Reaction equation

HRID 1943216 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C@H:9]2[N:19]3[C:20]4[N:11]([C:12](=[O:22])[CH:13]=[CH:14][C:15]=4[CH:16]=[CH:17][C:18]3=[O:21])[CH2:10]2)[CH2:4][CH2:3]1.[Cl:23][C:24]1[N:25]=[C:26]([CH:35]=O)[NH:27][C:28]2[C:29]=1[O:30][CH2:31][C:32](=[O:34])[N:33]=2.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CO>[Cl:23][C:24]1[N:25]=[C:26]([CH2:35][NH:1][CH:2]2[CH2:3][CH2:4][N:5]([CH2:8][C@H:9]3[N:19]4[C:20]5[N:11]([C:12](=[O:22])[CH:13]=[CH:14][C:15]=5[CH:16]=[CH:17][C:18]4=[O:21])[CH2:10]3)[CH2:6][CH2:7]2)[NH:27][C:28]2[C:29]=1[O:30][CH2:31][C:32](=[O:34])[N:33]=2

Participants

8

Reactant 5

HCID 24436Sodium SulfateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 58001796(1R)-1-[(4-amino-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dioneHCID 1785199864-Chloro-7-oxo-6,7-dihydro-1H-pyrimido[5,4-b][1,4]oxazine-2-carbaldehyde

Product 1

HCID 178516866HCID 178516866, compoundYield 4.51%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

In a 10 mL round-bottomed flask were combined (1R)-1-[(4-amino-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione (for a preparation see Example 5A(j)) (60 mg, 0.178 mmol), 4-chloro-7-oxo-6,7-dihydro-1H-pyrimido[5,4-b][1,4]oxazine-2-carbaldehyde (for a synthesis see WO2008009700, Example 124 (g)) (38 mg, 0.178 mmol), and sodium bicarbonate (150 mg, 1.78 mmol) in DCM (5 ml) and methanol (1 ml) to give a brown solution. Sodium sulfate (200 mg, 1.408 mmol) was added and the reaction was allowed to stir at rt overnight. After 15 h sodium triacetoxyborohydride (113 mg, 0.533 mmol) was added and the reaction was allowed to stir at 25° C. under nitrogen for 4 h. The reaction mixture was adsorbed onto silica and purified using 0-20% MeOH/DCM (1% NH4OH) to give the title compound (4 mg orange solid, 4.51%).

Workup

  1. customIn a 10 mL round-bottomed flask were combined
  2. customto give a brown solution
  3. stirringto stir at 25° C. under nitrogen for 4 h
  4. custompurified

Sources & evidence

ORD record
ord-0e3452634aab4fc798dd33bd6028f6d3
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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