1,2-Dichloroethane → 2-({[4-(4-Chlorophenyl)-2-oxo-3-(3,3,3-trifluoro-2-hydroxypropyl)-2,3-dihydro-1H-imidazol-1-yl]acetyl}amino)-2-[3-(trifluoromethyl)phenyl]ethyl carbamate

HRID 2402850Notes

Reaction equation

HRID 2402850 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:18][CH:19]([OH:24])[C:20]([F:23])([F:22])[F:21])[C:10](=[O:17])[N:11]([CH2:13][C:14](O)=[O:15])[CH:12]=2)=[CH:4][CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[C:39](=[O:53])([O:41][CH2:42][CH:43]([NH2:52])[C:44]1[CH:49]=[CH:48][CH:47]=[C:46](Cl)[C:45]=1Cl)[NH2:40].Cl>CN(C=O)C>[C:39](=[O:53])([O:41][CH2:42][CH:43]([NH:52][C:14](=[O:15])[CH2:13][N:11]1[CH:12]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]([CH2:18][CH:19]([OH:24])[C:20]([F:23])([F:22])[F:21])[C:10]1=[O:17])[C:44]1[CH:49]=[CH:48][CH:47]=[C:46]([C:20]([F:23])([F:22])[F:21])[CH:45]=1)[NH2:40]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 59536810HCID 59536810, compoundHCID 595368632-Amino-2-(2,3-dichlorophenyl)ethyl carbamate

Product 1

HCID 595367762-({[4-(4-Chlorophenyl)-2-oxo-3-(3,3,3-trifluoro-2-hydroxypropyl)-2,3-dihydro-1H-imidazol-1-yl]acetyl}amino)-2-[3-(trifluoromethyl)phenyl]ethyl carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A quantity of 58 mg (0.11 mmol) of [4-(4-chlorophenyl)-2-oxo-3-(3,3,3-trifluoro-2-hydroxypropyl)-2,3-dihydro-1H-imidazol-1-yl]acetic acid from Example 184A was dissolved in 2 ml of DMF, and the solution was admixed with 28 mg (0.15 mmol) of EDC and with 20 mg (0.15 mmol) of HOBt and subsequently stirred at room temperature for 20 minutes. Then 42 mg (0.12 mmol) of the compound from Example 183A were added and the mixture was left with stirring at room temperature for 16 h. For work-up, 100 μl of 1N hydrochloric acid were added and the crude product was purified directly by preparative HPLC [Method 19]. This gave 13 mg (18% of theory) of the target compound.

Workup

  1. waitthe mixture was left
  2. stirringwith stirring at room temperature for 16 h
  3. customthe crude product was purified directly by preparative HPLC [Method 19]

Sources & evidence

ORD record
ord-95ff1dd4da69480f8e6504f82c5d0983
Source dataset
uspto-grants-2014_08
Patent number
US08796324B2

Reaction notes

Loading…