4-Methylmorpholine → N-(4-tert-butyl-benzyl)-2,5-dichloro-N-[2-(3,4-dichloro-phenyl)-ethyl]-nicotinamide

HRID 2244374Notes

Reaction equation

HRID 2244374 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.[C:12]([C:16]1[CH:33]=[CH:32][C:19]([CH2:20][NH:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=2)=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13].CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:12]([C:16]1[CH:33]=[CH:32][C:19]([CH2:20][N:21]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=2)[C:4](=[O:6])[C:3]2[CH:7]=[C:8]([Cl:11])[CH:9]=[N:10][C:2]=2[Cl:1])=[CH:18][CH:17]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27360852,5-Dichloropyridine-3-carboxylic acidHCID 68563688(4-Tert-butylbenzyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amine

Product 1

HCID 24738250N-(4-tert-butyl-benzyl)-2,5-dichloro-N-[2-(3,4-dichloro-phenyl)-ethyl]-nicotinamideYield 95.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2,5-dichloronicotinic acid (300 mg, 1.56 mmol), (4-tert-butyl-benzyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amine (578 mg, 1.72 mmol), 4-methylmorpholine (474 mg, 7.81 mmol), and HBTU (889 mg, 2.34 mmol) in DMF (9 mL) was stirred at RT for 16 h, then partitioned between heptane, ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient) afforded the title compound (761 mg, 95%). White foam, MS (ISP) 509.0 (M+H)+.

Workup

  1. custompartitioned between heptane, ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-0da23c2f69f14ec7a591012551aae49a
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

Loading…