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

HRID 536554Notes

Reaction equation

HRID 536554 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:11](=[O:16])[N:10]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([OH:26])=O)=[CH:20][C:19]=3[O:27][CH3:28])[N:9]=2)=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[CH3:43][C:44]([NH2:47])([CH3:46])[CH3:45]>CN(C=O)C.O>[C:44]([NH:47][C:24]([C:21]1[CH:22]=[CH:23][C:18]([CH2:17][N:10]2[C:11](=[O:16])[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[N:9]2)=[C:19]([O:27][CH3:28])[CH:20]=1)=[O:26])([CH3:46])([CH3:45])[CH3:43]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6385Tert-ButylamineHCID 757711-HydroxybenzotriazoleHCID 584601334-{[3-(4-Chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}-3-methoxybenzenecarboxylic acid

Product 1

HCID 67430468N-tert-Butyl-4-{[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}-3-methoxybenzenecarboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

An amount of 50 mg (0.13 mmol) of the compound from Example 21A was introduced in 1 ml of DMF and admixed with 20 mg (0.15 mmol) of HOBt and with 31 mg (0.16 mmol) of EDC. After 10 minutes of stirring at RT, 14.5 μl (0.14 mmol) of 2-methylpropan-2-amine were added and the mixture was stirred further at room temperature for 16 h. Subsequently the reaction solution was diluted with about 5 ml of water and the precipitate formed was filtered and washed with water. Drying under reduced pressure gave 37 mg (66% of theory) of the target compound.

Workup

  1. stirringthe mixture was stirred further at room temperature for 16 h
  2. customthe precipitate formed
  3. filtrationwas filtered
  4. washwashed with water
  5. customDrying under reduced pressure
  6. customgave 37 mg (66% of theory) of the target compound

Sources & evidence

ORD record
ord-ba0f8b7fad5e4d5f97a40c074d418b3a
Source dataset
uspto-grants-2014_10
Patent number
US08859601B2

Reaction notes

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