Hydrochloric Acid → Ethyl[3-(3-{(3,3-diphenylpropyl) [(2e)-3-(4-pyridinyl)-2-propenoyl]amino}propyl)phenoxy]acetate

HRID 2389386Notes

Reaction equation

HRID 2389386 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/[C:9]([OH:11])=O)=[CH:3][CH:2]=1.C1C=CC2N(O)N=NC=2C=1.[CH2:22]([O:24][C:25](=[O:53])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH2:34][CH2:35][CH2:36][NH:37][CH2:38][CH2:39][CH:40]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:29]=1)[CH3:23].Cl>CN(C=O)C.CCOC(C)=O>[CH2:22]([O:24][C:25](=[O:53])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH2:34][CH2:35][CH2:36][N:37]([CH2:38][CH2:39][CH:40]([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:9](=[O:11])/[CH:8]=[CH:7]/[C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)[CH:29]=1)[CH3:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 7367823-(4-Pyridine)acrylic acidHCID 86637891Ethyl (3-{3-[(3,3-diphenylpropyl)amino]propyl}phenoxy)acetate

Product 1

HCID 59145338Ethyl[3-(3-{(3,3-diphenylpropyl) [(2e)-3-(4-pyridinyl)-2-propenoyl]amino}propyl)phenoxy]acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2E)-3-(4-pyridinyl)acrylic acid (23 mg) in DMF (1 mL) was added HOBt (21 mg), ethyl(3-{3-[(3,3-diphenylpropyl)amino]propyl}phenoxy)acetate (55 mg) and WSCD.HCl (29 mg) at ambient temperature. The reaction mixture was stirred for 8 hours at the same temperature. The resulting mixture was diluted with EtOAc and washed successively with water and brine. The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=85:15-70:30) to give a ethyl[3-(3-{(3,3-diphenylpropyl) [(2E)-3-(4-pyridinyl)-2-propenoyl]amino}propyl)phenoxy]acetate.

Workup

  1. customat ambient temperature
  2. washwashed successively with water and brine
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=85:15-70:30)

Sources & evidence

ORD record
ord-7e4c7a124d984228927329713844a2ff
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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