Diisopropylethylamine → N-(4-amino-2-oxo-1,2-dihydropyridin-3-yl)-2-(phenylamino)quinoline-8-carboxamide

HRID 1056009Notes

Reaction equation

HRID 1056009 reaction equation
[C:1]1([NH:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[C:11]([C:18]([OH:20])=[O:19])[CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:21][C:22]1[C:23](=[O:29])[NH:24][CH:25]=[CH:26][C:27]=1[NH2:28].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C>CN(C=O)C.C(Cl)(Cl)Cl.CC(O)C>[NH2:21][C:22]1[C:23](=[O:29])[NH:24][CH:25]=[CH:26][C:27]=1[NH:28][C:18]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[N:9]=[C:8]([NH:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH:17]=[CH:16]2)=[O:20].[NH2:28][C:27]1[CH:26]=[CH:25][NH:24][C:23](=[O:29])[C:22]=1[NH:21][C:18]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[N:9]=[C:8]([NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH:17]=[CH:16]2)=[O:19]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 234236693,4-Diaminopyridin-2-olHCID 897820232-(Phenylamino)quinoline-8-carboxylic acid

Product 2

HCID 89781868N-(4-amino-2-oxo-1,2-dihydropyridin-3-yl)-2-(phenylamino)quinoline-8-carboxamideHCID 89782101N-(3-amino-2-oxo-1,2-dihydropyridin-4-yl)-2-(phenylamino)quinoline-8-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21906603Chloroform isopropyl alcoholSolvent

Procedure

A mixture of 2-(phenylamino)quinoline-8-carboxylic acid (0.42 g, 1.589 mmol), 3,4-diaminopyridin-2(1H)-one (0.199 g, 1.589 mmol, Sphinx Scientific Laboratory LLC, Sycamore, Ill.), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate (V) (0.604 g, 1.589 mmol), and N-ethyl-N-isopropylpropan-2-amine (0.277 ml, 1.589 mmol) in DMF (1.589 ml) was stirred at RT for 2 h. The reaction was diluted with (3:2) CHCl3/IPA (200 ml), added to a separatory funnel, and washed with water (2×50 ml) before the organic layer was separated, dried over Na2SO4, and concentrated to give N-(3-amino-2-oxo-1,2-dihydropyridin-4-yl)-2-(phenylamino)quinoline-8-carboxamide (or N-(4-amino-2-oxo-1,2-dihydropyridin-3-yl)-2-(phenylamino)quinoline-8-carboxamide; regiochemistry not established) as a brown amorphous solid. MS (ESI, pos. ion) m/z: 372.2 (M+1).

Workup

  1. additionadded to a separatory funnel
  2. washwashed with water (2×50 ml) before the organic layer
  3. customwas separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-669d8b554fb34ab4a78f6782e34b72d8
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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