Ammonia → 5-Fluoro-1-[[4-(1H-imidazol-1-yl)phenyl]methyl]-3-methyl-1H-indole-2-propanamide

HRID 5946Notes

Reaction equation

HRID 5946 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]3[CH:22]=[CH:21][N:20]=[CH:19]3)=[CH:14][CH:13]=1)[C:6]([CH2:23][CH2:24][C:25]([OH:27])=O)=[C:5]2[CH3:28].O=S(Cl)Cl.[NH3:33]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]3[CH:22]=[CH:21][N:20]=[CH:19]3)=[CH:14][CH:13]=1)[C:6]([CH2:23][CH2:24][C:25]([NH2:33])=[O:27])=[C:5]2[CH3:28]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 97998665-Fluoro-1-[[4-(1H-imidazol-1-yl)phenyl]methyl]-3-methyl-1H-indole-2-propanoic acid

Product 1

HCID 197946705-Fluoro-1-[[4-(1H-imidazol-1-yl)phenyl]methyl]-3-methyl-1H-indole-2-propanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 5-fluoro-1-[[4-(1H-imidazol-1-yl)phenyl]methyl]-3-methyl-1H-indole-2-propanoic acid (1.0 g) in DMF (10 ml) is treated with SOCl2 (0.5 g) and, after cooling a gaseous NH3 is passed through the reaction mixture for 6 hours. The ammonium salt is filtered off and ether is added to the solution. The so obtained precipitated is filtered and dried to give 0.8 g of the title compound.

Workup

  1. filtrationThe ammonium salt is filtered off
  2. additionether is added to the solution
  3. customThe so obtained
  4. customprecipitated
  5. filtrationis filtered
  6. customdried

Sources & evidence

ORD record
ord-9a8ff7f9ad0e479a86acac8c6fa85654
Source dataset
uspto-grants-1993_09
Patent number
US05246957

Reaction notes

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