Acetic Anhydride → N-{2-Acetamido-2-[3-(trifluoromethyl)phenyl]ethyl}-2-{3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetamide

HRID 709156Notes

Reaction equation

HRID 709156 reaction equation
C(N(CC)C(C)C)(C)C.Cl.[NH2:11][CH:12]([C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([F:47])([F:46])[F:45])[CH:39]=1)[CH2:13][NH:14][C:15](=[O:37])[CH2:16][N:17]1[C:21](=[O:22])[N:20]([CH2:23][C@H:24]([OH:29])[C:25]([F:28])([F:27])[F:26])[C:19]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)=[N:18]1.[C:48](OC(=O)C)(=[O:50])[CH3:49]>ClCCl>[C:48]([NH:11][CH:12]([C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([F:47])([F:46])[F:45])[CH:39]=1)[CH2:13][NH:14][C:15](=[O:37])[CH2:16][N:17]1[C:21](=[O:22])[N:20]([CH2:23][C@H:24]([OH:29])[C:25]([F:28])([F:27])[F:26])[C:19]([C:30]2[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=2)=[N:18]1)(=[O:50])[CH3:49]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 89765105N-{2-Amino-2-[3-(trifluoromethyl)phenyl]ethyl}-2-{3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetamide hydrochloride

Product 1

HCID 87085259N-{2-Acetamido-2-[3-(trifluoromethyl)phenyl]ethyl}-2-{3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

20 μl (0.11 mmol) of N,N-diisopropylethylamine were added to a solution of 60 mg (0.10 mmol) of the compound of Example 58A in 1 ml of dichloromethane. The mixture was cooled to 0° C., 10 μl (0.10 mmol) of acetic anhydride were then added and stirring was continued at 0° C. for 1 h. The volatile components were then removed on a rotary evaporator. The residue was dissolved in a little DMSO and separated by preparative HPLC [Method 8]. The product-containing fraction was freed from the solvent on a rotary evaporator and the residue was dried under high vacuum. This gave 50 mg (83% of theory) of the title compound.

Workup

  1. customThe volatile components were then removed on a rotary evaporator
  2. dissolutionThe residue was dissolved in a little DMSO
  3. customseparated by preparative HPLC [Method 8]
  4. customThe product-containing fraction was freed from the solvent on a rotary evaporator
  5. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-4d2f4be0aa7b40dba4832ea505927bb4
Source dataset
uspto-grants-2015_11
Patent number
US09180120B2

Reaction notes

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