4-Methylmorpholine → HCID 178487704, compound

HRID 2044020Notes

Reaction equation

HRID 2044020 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].[Cl-].[NH4+].C[N:21](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[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]([NH2:21])=[O:13])[CH:8]=[C:7]2[OH:15]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 25517Ammonium Chloride2×HCID 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 178487704HCID 178487704, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-Chloro-4-hydroxy-7-methoxy-quinoline-2-carboxylic acid (115 mg, 0.45 mmol) and ammoniumchloride (36 mg, 0.68 mmol) were dissolved in DMF (4 mL). HATU (342 mg, 0.9 mmol) and NMM (159 mg, 1.58 mmol) were added and the mixture was stirred at r.t. overnight. An additional amount of ammoniumchloride (72 mg, 13.5 mmol) was added and heated to 53° C. for 18 h. The reaction mixture was cooled to r.t. and concentrated to give 8-chloro-4-hydroxy-7-methoxy-quinoline-2-carboxylic acid amide as a yellow solid.

Workup

  1. temperatureheated to 53° C. for 18 h
  2. temperatureThe reaction mixture was cooled to r.t.
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c757f5ea7257429794f94baf93d54080
Source dataset
uspto-grants-2013_11
Patent number
US08586744B2

Reaction notes

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