Ethylmorpholine → N-((tetrahydro-2H-pyran-4-yl)methyl)-2-((1-(4-(trifluoromethyl)benzyl)-3-((((4-(trifluoromethyl)benzyl)oxy)imino)methyl)-1H-indol-5-yl)oxy)acetamide

HRID 68327Notes

Reaction equation

HRID 68327 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]1[CH:37]=[CH:36][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19](O)=[O:20])=[CH:14][CH:15]=3)[C:10]([CH:22]=[N:23][O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)=[CH:9]2)=[CH:5][CH:4]=1.Cl.[O:41]1[CH2:46][CH2:45][CH:44]([CH2:47][NH2:48])[CH2:43][CH2:42]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.C(N1CCOCC1)C>CN(C=O)C>[O:41]1[CH2:46][CH2:45][CH:44]([CH2:47][NH:48][C:19](=[O:20])[CH2:18][O:17][C:13]2[CH:12]=[C:11]3[C:16](=[CH:15][CH:14]=2)[N:8]([CH2:7][C:6]2[CH:36]=[CH:37][C:3]([C:2]([F:38])([F:39])[F:1])=[CH:4][CH:5]=2)[CH:9]=[C:10]3[CH:22]=[N:23][O:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:33])[F:34])=[CH:28][CH:27]=2)[CH2:43][CH2:42]1

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 44118690(Oxan-4-yl)methanamine hydrochlorideHCID 76528216HCID 76528216, compound

Product 1

HCID 76528446N-((tetrahydro-2H-pyran-4-yl)methyl)-2-((1-(4-(trifluoromethyl)benzyl)-3-((((4-(trifluoromethyl)benzyl)oxy)imino)methyl)-1H-indol-5-yl)oxy)acetamideYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound prepared in example 8 (250 mg, 0.454 mmoles) in DMF (2 mL), (tetrahydro-2H-pyran-4-yl)methanamine hydrochloride (83 mg, 0.545 mmoles), HOBT (Catalyst), EDC.HCl (130 mg, 0.681 mmoles) and N-ethyl morpholine (0.173 ml, 1.362 mmoles) were added and the 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 evaporated under reduced pressure. The crude product was purified by column chromatography to yield 200 mg (68%) of product as white solid.

Workup

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

Sources & evidence

ORD record
ord-75460e64c3064df2b069acc18a7b9421
Source dataset
uspto-grants-2014_09
Patent number
US08822414B2

Reaction notes

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