1,2-Dichloroethane → HCID 57991969, compound

HRID 2075334Notes

Reaction equation

HRID 2075334 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[Cl:38][C:39]1[CH:44]=[N:43][CH:42]=[C:41]2[S:45][C:46]([C:48]3[S:52][C:51]([NH2:53])=[N:50][N:49]=3)=[CH:47][C:40]=12.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:38][C:39]1[CH:44]=[N:43][CH:42]=[C:41]2[S:45][C:46]([C:48]3[S:52][C:51]([NH:53][C:10](=[O:11])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:4])[CH3:2])[CH2:13][C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=4)=[N:50][N:49]=3)=[CH:47][C:40]=12

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 7020838N-[tert-Butoxy(hydroxy)methylidene]-3-(trifluoromethyl)phenylalaninatoHCID 57991954HCID 57991954, compound

Product 1

HCID 57991969HCID 57991969, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-2-((tert-Butoxycarbonyl)amino)-3-(3-(trifluoromethyl)phenyl)propanoic acid (1 g, 3 mmol) purchased from Peptech was mixed with EDC (0.766 g, 4 mmol) and HOBt (0.810 g, 6 mmol) in 5 mL DMF in a round bottom flask. The mixture was stirred at room temperature for 30 minutes. 5-(4-Chlorothieno[2,3-c]pyridin-2-yl)-1,3,4-thiadiazol-2-amine (0.268 g, 1 mmol) was added to the flask followed by addition of DIEA (1.4 mL, 8 mmol). The mixture was heated at 50° C. for one hour. After the DMF was removed under reduced pressure, the remaining residue was mixed with 200 mL EtOAc. The EtOAc solution was washed three times with saturated ammonium chloride aqueous solution, three times with saturated aqueous NaHCO3, and then dried over Na2SO4. After removing the solvent, the product was obtained and used directly in the next step.

Workup

  1. temperatureThe mixture was heated at 50° C. for one hour
  2. customAfter the DMF was removed under reduced pressure
  3. additionthe remaining residue was mixed with 200 mL EtOAc
  4. washThe EtOAc solution was washed three times with saturated ammonium chloride aqueous solution, three times with saturated aqueous NaHCO3
  5. dry with materialdried over Na2SO4
  6. customAfter removing the solvent
  7. customthe product was obtained

Sources & evidence

ORD record
ord-57f2b07691d343e09cb422de8eb1dbf0
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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