Ethylmorpholine → 2,2'-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)oxazol-2-yl)azanediyl)bis(N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide)

HRID 68322Notes

Reaction equation

HRID 68322 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:27]=[CH:26][C:6]([CH2:7][O:8][N:9]=[C:10]([C:12]2[O:16][C:15]([N:17]([CH2:22][C:23]([OH:25])=O)[CH2:18][C:19]([OH:21])=O)=[N:14][CH:13]=2)[CH3:11])=[CH:5][CH:4]=1.[O:30]1[CH2:35][CH2:34][CH:33]([CH2:36][NH2:37])[CH2:32][CH2:31]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=N[CH2:53][CH2:54][CH2:55][N:56](C)C.Cl.C(N1C[CH2:66][O:65][CH2:64][CH2:63]1)C>CN(C=O)C>[F:29][C:2]([F:1])([F:28])[C:3]1[CH:27]=[CH:26][C:6]([CH2:7][O:8][N:9]=[C:10]([C:12]2[O:16][C:15]([N:17]([CH2:22][C:23]([NH:56][CH2:55][CH:54]3[CH2:53][CH2:66][O:65][CH2:64][CH2:63]3)=[O:25])[CH2:18][C:19]([NH:37][CH2:36][CH:33]3[CH2:34][CH2:35][O:30][CH2:31][CH2:32]3)=[O:21])=[N:14][CH:13]=2)[CH3:11])=[CH:5][CH:4]=1

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27732104-AminomethyltetrahydropyranHCID 765282152,2'-((5-(1-(((4-(Trifluoromethyl)benzyl)oxy)imino)ethyl)oxazol-2-yl)azanediyl)diacetic acid

Product 1

HCID 765284452,2'-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)oxazol-2-yl)azanediyl)bis(N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide)Yield 49.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound prepared in example 6 (250 mg, 0.60 mmoles) in DMF (2 mL), (tetrahydro-2H-pyran-4-yl)methanamine (138 mg, 1.20 mmoles), HOBT (121 mg, 0.90 mmoles), EDC.HCl (138 mg, 0.72 mmoles) and N-ethyl morpholine (227 μL, 1.80 mmoles) were added and reaction mixture was srirred at 25° C. for 2-5 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 evaporated under reduced pressure. The crude product was triturated with hexane to yield 180 mg (49%) 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. customevaporated under reduced pressure
  8. customThe crude product was triturated with hexane

Sources & evidence

ORD record
ord-c689f77a9752451b98bc9ba6fd90e553
Source dataset
uspto-grants-2014_09
Patent number
US08822414B2

Reaction notes

Loading…