Hydrochloric Acid → HCID 178487705, compound

HRID 1367733Notes

Reaction equation

HRID 1367733 reaction equation
[Cl:1][C:2]1[C:3]([O:16][CH3:17])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12](O)=[O:13])[CH:8]=[C:7]2[OH:15].[CH3:18][NH:19][CH3:20].C1COCC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.Cl>CN(C=O)C.CCOC(C)=O>[CH3:18][N:19]([CH3:20])[C:12]([C:9]1[CH:8]=[C:7]([OH:15])[C:6]2[C:11](=[C:2]([Cl:1])[C:3]([O:16][CH3:17])=[CH:4][CH:5]=2)[N:10]=1)=[O:13]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 79724-MethylmorpholineHCID 8028TetrahydrofuranHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178487707HCID 178487707, compound

Product 1

HCID 178487705HCID 178487705, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The 8-chloro-4-hydroxy-7-methoxy-quinoline-2-carboxylic acid (500 mg, 1.97 mmol) and 2.0 M dimethylamine in THF (2 mL, 3.94 mmol) were dissolved in DMF (20 mL). HATU (1.5 g, 3.94 mmol) and NMM (697 mg, 6.89 mmol) were added and the mixture was stirred at r.t. overnight. The reaction was diluted with EtOAc and acidified with 1 N HCl. The two layers were separated. The organic layer was washed with 2% LiCl, saturated NaHCO3 and brine, dried with Na2SO4, and concentrated to give 8-chloro-4-hydroxy-7-methoxy-quinoline-2-carboxylic acid dimethylamide.

Workup

  1. customThe two layers were separated
  2. washThe organic layer was washed with 2% LiCl, saturated NaHCO3 and brine
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-720a583a8f5c4279b3bda299a1ff6a80
Source dataset
uspto-grants-2011_02
Patent number
US07893264B2

Reaction notes

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