Triethylamine → 4-bromo-N-methoxy-N-methylquinoline-6-carboxamide

HRID 1778299Notes

Reaction equation

HRID 1778299 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([OH:14])=O)[CH:10]=2)[N:5]=[CH:4][CH:3]=1.CN([C:18]([O:22][N:23]1N=NC2C=CC=N[C:24]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>C(Cl)Cl.O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([N:23]([O:22][CH3:18])[CH3:24])=[O:14])[CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 223880974-Bromoquinoline-6-carboxylic acid

Product 1

HCID 1183240674-bromo-N-methoxy-N-methylquinoline-6-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 4-bromoquinoline-6-carboxylic acid (5 g), CH3ONH(CH3) hydrochloride salt (1.8 eq. 3.5 g), and HATU (1.15 eq. 8.67 g) in CH2Cl2 (100 mL) was slowly added triethylamine (4 eq. 11 mL) at 0° C. and the resulting reaction mixture was stirred at room temperature overnight. The reaction was diluted with CH2Cl2 and water. The combined organics were washed with water several times, concentrated and then purified by chromatography (60-70% EtOAc/hexanes) to yield 4-bromo-N-methoxy-N-methylquinoline-6-carboxamide as a white solid.

Workup

  1. customat 0° C.
  2. customthe resulting reaction mixture
  3. washThe combined organics were washed with water several times
  4. concentrationconcentrated
  5. custompurified by chromatography (60-70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b8d6dc208a804b06bc8dd84132d449ba
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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