1,2-Dichloroethane → HCID 86720681, compound

HRID 1844548Notes

Reaction equation

HRID 1844548 reaction equation
C1C=CC2N(O)N=NC=2C=1.[CH3:11][O:12][C:13]1[C:18]([C:19]2[CH:24]=[CH:23][C:22]([S:25](=[O:28])(=[O:27])[NH2:26])=[CH:21][CH:20]=2)=[CH:17][C:16]([C:29]2[S:33][C:32]([C:34](O)=[O:35])=[N:31][C:30]=2[CH3:37])=[CH:15][CH:14]=1.Cl.[CH3:39][NH:40][O:41][CH3:42].C(Cl)CCl.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[CH3:42][O:41][N:40]([CH3:39])[C:34]([C:32]1[S:33][C:29]([C:16]2[CH:17]=[C:18]([C:19]3[CH:20]=[CH:21][C:22]([S:25](=[O:28])(=[O:27])[NH2:26])=[CH:23][CH:24]=3)[C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)=[C:30]([CH3:37])[N:31]=1)=[O:35]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 71203599HCID 71203599, compound

Product 1

HCID 86720681HCID 86720681, compoundYield 37.23%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

HOBT (0.62 g, 4.62 mmol) was added to a solution of 5-(6-methoxy-4′-sulfamoyl-[1,1′-biphenyl]-3-yl)-4-methylthiazole-2-carboxylic acid (8b, 1.70 g, 4.20 mmol) in DMF (15 ml) at room temperature under stirring. N,O-dimethylhydroxylamine hydrochloride (0.82 g, 8.40 mmol) was then added to the reaction mixture. The reaction mixture was cooled to 0° C. and to this were added EDC (1.20 g, 6.31 mmol) and triethylamine (1.69 g, 2.34 ml, 16.80 mmol). The reaction mixture was stirred at room temperature for 15 hours. The progress of the reaction was monitored by TLC. The reaction mixture was then concentrated under reduced pressure. The residue so obtained was mixed with ethyl acetate (100 ml). The mixture obtained was washed with saturated sodium bicarbonate solution (20 ml) followed by washing with brine (20 ml). The separated organic layer was dried over anhydrous sodium sulphate. The dried organic layer was then concentrated under reduced pressure to obtain a crude product. The crude product was then purified by column chromatography using 50% ethyl acetate in hexanes as an eluent to obtain the title compound 8c (0.70 g, 37.23%).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 15 hours
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. customThe residue so obtained
  4. customThe mixture obtained
  5. washwas washed with saturated sodium bicarbonate solution (20 ml)
  6. washby washing with brine (20 ml)
  7. dry with materialThe separated organic layer was dried over anhydrous sodium sulphate
  8. concentrationThe dried organic layer was then concentrated under reduced pressure
  9. customto obtain a crude product
  10. customThe crude product was then purified by column chromatography

Sources & evidence

ORD record
ord-3527ad02fa9a4e919754ec8d4a571e3f
Source dataset
uspto-grants-2015_02
Patent number
US08946432B2

Reaction notes

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