Triethylamine → HCID 22936668, compound

HRID 387978Notes

Reaction equation

HRID 387978 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:20][CH3:21])=[C:14]([C:17](O)=[O:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:4][C:3]=1[N+:24]([O-:26])=[O:25].CN.CO.[CH2:31]([N:33](CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C)C=O.O.C(OCC)(=O)C>[CH3:31][NH:33][C:17]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[O:20][CH3:21])[N:10]=[CH:9][CH:8]=[C:7]2[O:6][C:5]1[CH:22]=[CH:23][C:2]([Cl:1])=[C:3]([N+:24]([O-:26])=[O:25])[CH:4]=1)=[O:18]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 22936444HCID 22936444, compoundHCID 57454252Monomethylamine methanol

Product 1

HCID 22936668HCID 22936668, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

After dissolving 4-(4-chloro-3-nitrophenoxy)-7-methoxy-6-quinolinecarboxylic acid (897 mg, 2.39 mmol) in dimethylformamide (10 ml) under a nitrogen atmosphere, a 40% methylamine-methanol solution (2.0 ml), triethylamine (1.0 ml) and (1H-1,2,3-benzotriazol-1-yloxy)(tri(dimethylamino)) phosphonium hexafluorophosphate (1.27 g, 2.87 mmol) were added in that order at room temperature and the mixture was stirred for 4 hours. The reaction solution was distributed between ethyl acetate and water, and the organic layer was washed with water and saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled off, the residue was suspended in ethyl acetate and diluted with hexane, and the crystals were filtered out and blow-dried to obtain the title compound (928 mg, quantitative) as white crystals.

Workup

  1. washthe organic layer was washed with water and saturated saline
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off
  4. additiondiluted with hexane
  5. filtrationthe crystals were filtered out and
  6. customblow-dried

Sources & evidence

ORD record
ord-53e65afe30ec41be8f7a304e49e9c8fa
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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