Dimethylformamide → HCID 59427300, compound

HRID 1042791Notes

Reaction equation

HRID 1042791 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.Cl[C:10]1[CH:11]=[CH:12][N:13]=[C:14]2[C:19]=1[N:18]=[CH:17][C:16]([O:20][CH3:21])=[CH:15]2.CN(C=O)C>CCOC(C)=O>[CH3:21][O:20][C:16]1[CH:15]=[C:14]2[C:19]([C:10]([S:8][C:5]3[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=3)=[CH:11][CH:12]=[N:13]2)=[N:18][CH:17]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 145104-AminothiophenolHCID 594273408-Chloro-3-methoxy-1,5-naphthyridine

Product 1

HCID 59427300HCID 59427300, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A RBF was charged with 4-aminothiophenol (161 mg, 1.285 mmol), 8-chloro-3-methoxy-1,5-naphthyridine (250 mg, 1.285 mmol) and 5.2 mL of DMF, and the mixture was stirred at RT for 45 min. The orange, heterogeneous mixture was diluted with EtOAc and washed with 1N NaHCO3. The aqueous portion was extracted two additional times with EtOAc and the combined organics were dried with MgSO4, filtered and concentrated. The crude oil was concentrated twice from toluene to remove DMF and the resulting solids were dried under high vacuum to provide 4-(7-methoxy-1,5-naphthyridin-4-ylthio)benzenamine as a tan solid. MS m/z=284 [M+H]+. Calc'd for C15H13N3OS: 283.35.

Workup

  1. washwashed with 1N NaHCO3
  2. extractionThe aqueous portion was extracted two additional times with EtOAc
  3. dry with materialthe combined organics were dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. concentrationThe crude oil was concentrated twice from toluene
  7. customto remove DMF
  8. customthe resulting solids were dried under high vacuum

Sources & evidence

ORD record
ord-8d8bb140f2d8427299a693c739677895
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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