1,2-Dichloroethane → 2-[({3-(4-Chlorophenyl)-5-oxo-4-[(1E)-3,3,3-trifluoroprop-1-en-1-yl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetyl)amino]-2-[3-(trifluoromethyl)phenyl]ethyl carbamate

HRID 2402837Notes

Reaction equation

HRID 2402837 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12](/[CH:13]=[CH:14]/[C:15]([F:18])([F:17])[F:16])[C:11](=[O:19])[N:10]([CH2:20][C:21](O)=[O:22])[N:9]=2)=[CH:4][CH:3]=1.Cl.[C:25](=[O:41])([O:27][CH2:28][CH:29]([NH2:40])[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=1)[NH2:26].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C.Cl>CN(C=O)C>[C:25](=[O:41])([O:27][CH2:28][CH:29]([NH:40][C:21](=[O:22])[CH2:20][N:10]1[C:11](=[O:19])[N:12](/[CH:13]=[CH:14]/[C:15]([F:18])([F:17])[F:16])[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[N:9]1)[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:37])[F:38])[CH:31]=1)[NH2:26]

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 59536906{3-(4-Chlorophenyl)-5-oxo-4-[(1E)-3,3,3-trifluoroprop-1-en-1-yl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetic acidHCID 686461642-Amino-2-[3-(trifluoromethyl)phenyl]ethyl carbamate hydrochloride

Product 1

HCID 595367322-[({3-(4-Chlorophenyl)-5-oxo-4-[(1E)-3,3,3-trifluoroprop-1-en-1-yl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetyl)amino]-2-[3-(trifluoromethyl)phenyl]ethyl carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Of the compound from Example 77A, 100 mg (0.29 mmol) were introduced in 3 ml of DMF and admixed with 98.3 mg (0.35 mmol) of the compound from Example 60A, 66.1 mg (0.35 mmol) of EDC, 49 mg (0.35 mmol) of HOBt and 75 μl (0.43 mmol) of N,N-diisopropylethylamine. The mixture was stirred at RT for 30 min and then admixed with 1 ml of 1N hydrochloric acid and purified by preparative HPLC (Method 10). This gave 140 mg (84% of theory) of the title compound.

Workup

  1. custompurified by preparative HPLC (Method 10)

Sources & evidence

ORD record
ord-1431d29cd3cd4ce1ac876a9791cf7515
Source dataset
uspto-grants-2014_08
Patent number
US08796324B2

Reaction notes

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