1,2-Dichloroethane → HCID 86669314, compound

HRID 2042843Notes

Reaction equation

HRID 2042843 reaction equation
[Cl:1][C:2]1[C:15]([N:16]=[C:17]=S)=[C:14]([Cl:19])[CH:13]=[CH:12][C:3]=1[CH2:4][NH:5][C:6](=[O:11])[C:7]([CH3:10])([CH3:9])[CH3:8].[CH3:20][O:21][C:22](=[O:36])[C:23]1[CH:28]=[C:27]([NH2:29])[C:26]([NH2:30])=[N:25][C:24]=1[O:31][CH2:32][CH:33]([F:35])[F:34].C(Cl)CCl>CC#N.O>[Cl:1][C:2]1[C:15]([NH:16][C:17]2[NH:29][C:27]3[C:26]([N:30]=2)=[N:25][C:24]([O:31][CH2:32][CH:33]([F:35])[F:34])=[C:23]([C:22]([O:21][CH3:20])=[O:36])[CH:28]=3)=[C:14]([Cl:19])[CH:13]=[CH:12][C:3]=1[CH2:4][NH:5][C:6](=[O:11])[C:7]([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 56840192N-[(2,4-dichloro-3-isothiocyanatophenyl)methyl]-2,2-dimethylpropanamideHCID 86664894HCID 86664894, compound

Product 1

HCID 86669314HCID 86669314, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of N-(2,4-dichloro-3-isothiocyanato-benzyl)-2,2-dimethyl-propionamide (4.00 g, 12.6 mmol) and 5,6-diamino-2-(2,2-difluoro-ethoxy)-nicotinic acid methyl ester (3.10 g, 12.5 mmol, prepared according to WO2010/034799) in MeCN (30 ml) is stirred for 2.5 h, then EDC (2.75 g, 14.3 mmol) is added and it is stirred at reflux for 15 min. The mixture is diluted with water, concentrated and extracted with DCM. The organic phase is dried with MgSO4, filtered and concentrated.

Workup

  1. stirringit is stirred
  2. temperatureat reflux for 15 min
  3. concentrationconcentrated
  4. extractionextracted with DCM
  5. dry with materialThe organic phase is dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-06751cc7edc94f198fbe9581d5a272d5
Source dataset
uspto-grants-2013_11
Patent number
US08586604B2

Reaction notes

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