Diisopropylethylamine → HCID 178522455, compound

HRID 1055999Notes

Reaction equation

HRID 1055999 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([C:12]([OH:14])=O)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:15][C:16]1[C:17]([OH:23])=[N:18][CH:19]=[CH:20][C:21]=1[OH:22].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.CCOC(C)=O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([C:12]([NH:15][C:16]3[C:17]([OH:23])=[N:18][CH:19]=[CH:20][C:21]=3[OH:22])=[O:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

7

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 190262012-Chloroquinoline-8-carboxylic acidHCID 1785080833-amino-2-hydroxy-1H-pyridin-4-one

Product 1

HCID 178522455HCID 178522455, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-chloroquinoline-8-carboxylic acid (0.42 g, 2.023 mmol), 3-aminopyridine-2,4-diol (Example 179b, 0.383 g, 3.03 mmol), HATU (1.154 g, 3.03 mmol), and N-ethyl-N-isopropylpropan-2-amine (1.083 ml, 6.07 mmol) in DMF (2.023 ml) was stirred at RT for 16 h. The mixture was diluted with EtOAc (200 ml), added to a separatory funnel, and washed with water (3×100 ml) before the organic layer was separated, dried over Na2SO4, and concentrated. Purification by silica gel (100% DCM to 4% MeOH/DCM) provided 2-chloro-N-(2,4-dihydroxypyridin-3-yl)quinoline-8-carboxamide (181b, 24% yield as a yellow solid). MS (ESI, pos. ion) m/z: 316.2 (M+1).

Workup

  1. additionadded to a separatory funnel
  2. washwashed with water (3×100 ml) before the organic layer
  3. customwas separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by silica gel (100% DCM to 4% MeOH/DCM)

Sources & evidence

ORD record
ord-b6f71e2ccdf04bee8957551ede2078a0
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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