Cyclopropylamine → HCID 25115390, compound

HRID 1921291Notes

Reaction equation

HRID 1921291 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[NH:11][C:12]([C:14]1[CH:19]=[CH:18][C:17](=[O:20])[N:16]([C:21]2[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:28])[CH:15]=1)=[O:13].CN(C(ON1N=NC2[CH:40]=[CH:41][CH:42]=[N:43]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1(N)CC1.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:43][CH:42]2[CH2:40][CH2:41]2)=[O:8])=[CH:4][C:3]=1[NH:11][C:12]([C:14]1[CH:19]=[CH:18][C:17](=[O:20])[N:16]([C:21]2[C:22]([Cl:28])=[CH:23][CH:24]=[CH:25][C:26]=2[Cl:27])[CH:15]=1)=[O:13]

Participants

6

Reactant 4

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67056852HCID 67056852, compound

Product 1

HCID 25115390HCID 25115390, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-3-({[1-(2,6-dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinyl]carbonyl}amino)benzoic acid (1.74 g) in DMF (17 mL) were added HATU (3.03 g), cyclopropanamine (680 mg) and iPr2NEt (3.08 g) successively at 0° C., and the mixture was stirred at room temperature for 16 hr under a nitrogen atmosphere. The mixture was partitioned between EtOAc (50 mL) and 1 M HCl (50 mL), and the precipitates produced were removed by filtration. The organic layer of the filtrate was separated and washed with 1 M HCl (50 mL), saturated aqueous NaHCO3 (50 mL×2) and brine successively, dried over MgSO4 and filtered. The filtrate was evaporated in vacuo, and the residue was triturated with a mixture of IPE and MeOH. The precipitates were collected by filtration, triturated with EtOH and collected by filtration to give N-{2-chloro-5-[(cyclopropylamino)carbonyl]phenyl}-1-(2,6-dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxamide (890 mg).

Workup

  1. customThe mixture was partitioned between EtOAc (50 mL) and 1 M HCl (50 mL)
  2. customthe precipitates produced
  3. customwere removed by filtration
  4. customThe organic layer of the filtrate was separated
  5. washwashed with 1 M HCl (50 mL), saturated aqueous NaHCO3 (50 mL×2) and brine successively
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe filtrate was evaporated in vacuo
  9. customthe residue was triturated with a mixture of IPE and MeOH
  10. filtrationThe precipitates were collected by filtration
  11. customtriturated with EtOH
  12. filtrationcollected by filtration

Sources & evidence

ORD record
ord-f6835848233f4ab1b8364da4a47e2dfe
Source dataset
uspto-grants-2012_05
Patent number
US08173684B2

Reaction notes

Loading…