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1,2-Dichloroethane → 4-(5-{3-[3-Ethyl-3-(3-hydroxy-phenyl)-azepan-1-yl]-3-oxo-propyl}-imidazol-1-ylmethyl)-2-fluoro-benzonitrile

HRID 429070
Notes
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Reaction equation

HRID 429070 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[C:12]([CH2:13][CH2:14][C:15]([OH:17])=O)=[CH:11][N:10]=[CH:9]2)=[CH:5][C:4]=1[F:20])#[N:2].[CH2:21]([C:23]1([C:30]2[CH:31]=[C:32]([OH:36])[CH:33]=[CH:34][CH:35]=2)[CH2:29][CH2:28][CH2:27][CH2:26][NH:25][CH2:24]1)[CH3:22].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CN1CCOCC1>CN(C=O)C>[CH2:21]([C:23]1([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([OH:36])[CH:31]=2)[CH2:29][CH2:28][CH2:27][CH2:26][N:25]([C:15](=[O:17])[CH2:14][CH2:13][C:12]2[N:8]([CH2:7][C:6]3[CH:18]=[CH:19][C:3]([C:1]#[N:2])=[C:4]([F:20])[CH:5]=3)[CH:9]=[N:10][CH:11]=2)[CH2:24]1)[CH3:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 6453793N-DesmethylmeptazinolHCID 183543083-[3-(4-cyano-3-fluoro-benzyl)-3H-imidazol-4-yl]-propionic Acid

Product 1

HCID 18354307
4-(5-{3-[3-Ethyl-3-(3-hydroxy-phenyl)-azepan-1-yl]-3-oxo-propyl}-imidazol-1-ylmethyl)-2-fluoro-benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[3-(4-Cyano-3-fluoro-benzyl)-3H-imidazol-4-yl]-propionic acid, as described above in Step E, (0.56 g, 0.78 mmol) and 3-(3-ethyl-azepan-3-yl)-phenol, as described above in Step J, (0.182 g, 0.78 mmol), HOBT (0.126 g, 0.936 mmol), EDC (0.179 g, 0.936 mmol) and N-methylmorpholine (0.257 mL, 2.34 mmol) were dissolved in DMF (15 mL) and stirred at ambient temperature for 18 h. The DMF was removed in vacuo and the residue was partitioned between EtOAc and saturated aqueous NaHCO3 solution. The organic layer was washed with H2O, brine, dried (MgSO4), filtered, and concentrated to give the title compound.

Workup

  1. customThe DMF was removed in vacuo
  2. customthe residue was partitioned between EtOAc and saturated aqueous NaHCO3 solution
  3. washThe organic layer was washed with H2O, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0e5f9eacc7174d699880c1ba3186aea6
Source dataset
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06316436B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes