Ethylmorpholine → N-((Tetrahydro-2H-pyran-4-yl)methyl)-2-((4-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)propyl)phenyl)amino)acetamide

HRID 68318Notes

Reaction equation

HRID 68318 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:25]=[CH:24][C:6]([CH2:7][O:8][N:9]=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][CH2:20][C:21]([OH:23])=O)=[CH:15][CH:14]=2)[CH2:11][CH3:12])=[CH:5][CH:4]=1.Cl.[O:29]1[CH2:34][CH2:33][CH:32]([CH2:35][NH2:36])[CH2:31][CH2:30]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.C(N1CCOCC1)C>CN(C=O)C>[O:29]1[CH2:34][CH2:33][CH:32]([CH2:35][NH:36][C:21](=[O:23])[CH2:20][NH:19][C:16]2[CH:15]=[CH:14][C:13]([C:10](=[N:9][O:8][CH2:7][C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:27])([F:1])[F:26])=[CH:25][CH:24]=3)[CH2:11][CH3:12])=[CH:18][CH:17]=2)[CH2:31][CH2:30]1

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 44118690(Oxan-4-yl)methanamine hydrochlorideHCID 86699626HCID 86699626, compound

Product 1

HCID 76528444N-((Tetrahydro-2H-pyran-4-yl)methyl)-2-((4-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)propyl)phenyl)amino)acetamideYield 15%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product of step 4 (6.5 g, 0.0171 moles) in DMF (40 mL), (tetrahydro-2H-pyran-4-yl)methanamine hydrochloride (2.6 gm, 0.0171 moles), HOBT (2.31 gm, 0.0171 moles), EDC.HCl (4.24 gm, 0.0222 moles) and N-ethyl morpholine (5.9 gm, 0.0513 moles) were added and reaction mixture was srirred at 25° C. for 5 hours under nitrogen atmosphere. The reaction mixture was poured into ice cold water and extracted with ethyl acetate. The combined ethyl acetate extract was washed with water & brine, dried over sodium sulphate and evapourated under reduced pressure. The crude product was purified by coloumn chromatography using 1% MeOH in chloroform as eluent to yield 1.22 g (15%) of product as white solid.

Workup

  1. customreaction mixture
  2. additionThe reaction mixture was poured into ice cold water
  3. extractionextracted with ethyl acetate
  4. extractionThe combined ethyl acetate extract
  5. washwas washed with water & brine
  6. dry with materialdried over sodium sulphate
  7. customThe crude product was purified by coloumn chromatography

Sources & evidence

ORD record
ord-2c04be296d37492eb4e04e0de090cb81
Source dataset
uspto-grants-2014_09
Patent number
US08822414B2

Reaction notes

Loading…