1,2-Dichloroethane → N-tert-Butyl-4-{[3-(4-chlorophenyl)-5-oxo-4-(3,3,3-trifluoro-2-hydroxypropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}benzamide

HRID 536556Notes

Reaction equation

HRID 536556 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH:14]([OH:19])[C:15]([F:18])([F:17])[F:16])[C:11](=[O:20])[N:10]([CH2:21][C:22]3[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=3)[N:9]=2)=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[CH3:45][C:46]([NH2:49])([CH3:48])[CH3:47]>CN(C=O)C.O>[C:46]([NH:49][C:26](=[O:27])[C:25]1[CH:29]=[CH:30][C:22]([CH2:21][N:10]2[C:11](=[O:20])[N:12]([CH2:13][CH:14]([OH:19])[C:15]([F:18])([F:16])[F:17])[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[N:9]2)=[CH:23][CH:24]=1)([CH3:48])([CH3:47])[CH3:45]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6385Tert-ButylamineHCID 757711-HydroxybenzotriazoleHCID 584601374-{[3-(4-Chlorophenyl)-5-oxo-4-(3,3,3-trifluoro-2-hydroxypropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}benzoic acid

Product 1

HCID 58460123N-tert-Butyl-4-{[3-(4-chlorophenyl)-5-oxo-4-(3,3,3-trifluoro-2-hydroxypropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

An amount of 50 mg (0.11 mmol) of the compound from Example 28A was introduced in 1 ml of DMF and admixed with 18 mg (0.14 mmol) of HOBt and with 28 mg (0.15 mmol) of EDC. After 10 minutes of stirring at RT, 13 μl (0.12 mmol) of 2-methylpropan-2-amine were added and the mixture was stirred at room temperature for 16 h. Subsequently the reaction solution was admixed with about 3 ml of water and extracted with twice 5 ml of ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by chromatography [Method 8]. This gave 31 mg (55% of theory) of the target compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 16 h
  2. extractionextracted with twice 5 ml of ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by chromatography [Method 8]

Sources & evidence

ORD record
ord-81102f03eebc459f9c48a6d223540279
Source dataset
uspto-grants-2014_10
Patent number
US08859601B2

Reaction notes

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