Diisopropylethylamine → HCID 59234679, compound

HRID 1921293Notes

Reaction equation

HRID 1921293 reaction equation
[C:1]([N:5]1[C:10](=[O:11])[CH:9]=[CH:8][C:7]([C:12]([OH:14])=O)=[CH:6]1)([CH3:4])([CH3:3])[CH3:2].[NH2:15][C:16]1[CH:17]=[C:18]([CH:25]=[CH:26][C:27]=1[CH3:28])[C:19]([NH:21][CH:22]1[CH2:24][CH2:23]1)=[O:20].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH:22]1([NH:21][C:19]([C:18]2[CH:25]=[CH:26][C:27]([CH3:28])=[C:16]([NH:15][C:12]([C:7]3[CH:8]=[CH:9][C:10](=[O:11])[N:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH:6]=3)=[O:14])[CH:17]=2)=[O:20])[CH2:24][CH2:23]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 119838543-amino-N-cyclopropyl-4-methylbenzamideHCID 61728949HCID 61728949, compound

Product 1

HCID 59234679HCID 59234679, compoundYield 47.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-tert-butyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid (30 mg) in DMF (0.6 mL) were added 3-amino-N-cyclopropyl-4-methylbenzamide (44 mg), HATU (88 mg) and iPr2NEt (89 mg), and the mixture was stirred under a nitrogen atmosphere at room temperature for 3 hr. The reaction mixture was diluted with EtOAc (3 mL) and the resulting mixture was washed with 1 M HCl (3 mL×2), water (3 mL), saturated aqueous NaHCO3 (3 mL) and brine successively, dried over MgSO4, filtered and evaporated in vacuo. The residue was purified by preparative thin layer chromatography eluting with 10% MeOH in CH2Cl2 to give N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-1-tert-butyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide (27 mg).

Workup

  1. washthe resulting mixture was washed with 1 M HCl (3 mL×2), water (3 mL), saturated aqueous NaHCO3 (3 mL) and brine successively
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by preparative thin layer chromatography
  6. washeluting with 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-fa703ea2aed14c76ade69c1e898dd1a2
Source dataset
uspto-grants-2012_05
Patent number
US08173684B2

Reaction notes

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