Sodium Sulfate → HCID 58369038, compound

HRID 2061177Notes

Reaction equation

HRID 2061177 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:8]([OH:10])=O)[CH2:7][CH2:6]1)=[O:4].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[O-]S([O-])(=O)=O.[Na+].[Na+].[CH3:51][N:52]1[C:61]2[C:56](=[CH:57][N:58]=[C:59]([CH3:62])[CH:60]=2)[CH:55]=[C:54]([C:63]2[CH:64]=[C:65]([NH:70]/[C:71](/[NH2:74])=[N:72]/O)[CH:66]=[CH:67][C:68]=2[CH3:69])[C:53]1=[O:75]>CN(C=O)C>[CH3:51][N:52]1[C:61]2[C:56](=[CH:57][N:58]=[C:59]([CH3:62])[CH:60]=2)[CH:55]=[C:54]([C:63]2[CH:64]=[C:65]([NH:70][C:71]3[N:72]=[C:8]([C:5]4([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH2:7]4)[O:10][N:74]=3)[CH:66]=[CH:67][C:68]=2[CH3:69])[C:53]1=[O:75]

Participants

7

Reactant 5

HCID 24436Sodium SulfateHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 138618231-(Methoxycarbonyl)cyclopropane-1-carboxylic acidHCID 178422078HCID 178422078, compound

Product 1

HCID 58369038HCID 58369038, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-(methoxycarbonyl)cyclopropanecarboxylic acid (56 mg, 0.39 mmol), HATU (180 mg, 0.47 mmol) and DIPEA (0.082 mL, 0.47 mmol) in dry DMF (2 mL) at rt in the presence of anhydrous Na2SO4 (284 mg, 2.0 mmol) was added 17 (130 mg, 0.39 mmol) slowly. The consumption of 17 was determined to be completed by LC/MS. The mixture was heated at 100° C. for 2 h. Solid was filtered off and the residue was dissolved in EtOAc (50 mL). The organic layer was washed with water twice, dried over Na2SO4, filtered and evaporated to yield a residue which was purified by flash chromatography on silica with 3-5% MeOH in DCM as eluant to yield methyl 1-(3-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenylamino)-1,2,4-oxadiazol-5-yl)cyclopropanecarboxylate 23. MS m/z 446.2 (M+1).

Workup

  1. customThe consumption of 17
  2. filtrationSolid was filtered off
  3. dissolutionthe residue was dissolved in EtOAc (50 mL)
  4. washThe organic layer was washed with water twice
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customto yield a residue which
  9. customwas purified by flash chromatography on silica with 3-5% MeOH in DCM as eluant

Sources & evidence

ORD record
ord-96b3c4fba1e44e9498a14a27f7343f30
Source dataset
uspto-grants-2012_10
Patent number
US08278452B2

Reaction notes

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