Ammonium Chloride → HCID 58011783, compound

HRID 660958Notes

Reaction equation

HRID 660958 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH:14]=[O:15])[C:11](=[O:16])[N:10]([CH2:17][C:18]([NH:20][C:21]([CH3:33])([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[CH3:22])=[O:19])[N:9]=2)=[CH:4][CH:3]=1.[CH:34]1([Mg]Br)[CH2:36][CH2:35]1.[Cl-].[NH4+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH:14]([CH:34]3[CH2:36][CH2:35]3)[OH:15])[C:11](=[O:16])[N:10]([CH2:17][C:18]([NH:20][C:21]([CH3:33])([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:30])([F:31])[F:32])[CH:24]=3)[CH3:22])=[O:19])[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 58011768HCID 58011768, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 58011783HCID 58011783, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

103 mg (0.21 mmol) of 2-[3-(4-chlorophenyl)-4-(2-oxoethyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-{1-methyl-1-[3-(trifluoromethyl)phenyl]ethyl}-acetamide from Example 401 are dissolved in 1 ml of THF and treated at −78° C. with 1.1 ml (0.54 mmol) of cyclopropylmagnesium bromide (0.5 M solution in THF). This is stirred for 3 hrs at RT and then for a further 2 hrs at 50° C. For the workup, it is treated with saturated ammonium chloride solution and extracted twice with 10 ml of ethyl acetate each time. The combined organic phases are dried over sodium sulphate, filtered and concentrated in vacuo. The crude product is purified by preparative HPLC [Method 10]. 12 mg (11% of theory) of the target compound are thus obtained.

Workup

  1. waitfor a further 2 hrs at 50° C
  2. extractionextracted twice with 10 ml of ethyl acetate each time
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by preparative HPLC [Method 10]
  7. custom12 mg (11% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-68e09c495a2e41c6b2f7ff955297ad3b
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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