Dicyclohexylcarbodiimide → HCID 86642295, compound

HRID 446910

Reaction equation

HRID 446910 reaction equation
[SH:1][C:2]1[N:3]([NH2:20])[C:4]([C@H:7]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:8])=[N:5][N:6]=1.[Cl:21][C:22]1[CH:23]=[C:24]([N:28]=[C:29]=S)[CH:25]=[CH:26][CH:27]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(O)C.CCOCC>[Cl:21][C:22]1[CH:23]=[C:24]([NH:28][C:29]2[S:1][C:2]3=[N:6][N:5]=[C:4]([C@H:7]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH3:8])[N:3]3[N:20]=2)[CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 754493-Chlorophenyl isothiocyanateHCID 178462184HCID 178462184, compound

Product 1

HCID 86642295HCID 86642295, compoundYield 48.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

(Step 8-ii) A mixture of (R)-benzyl 1-(5-mercapto-4-amino-4H-1,2,4-triazol-3-yl)ethylcarbamate (1.32 g, 4.5 mmol) in ethanol (15 mL) was heated to 80° C. and 3-chlorophenylisothiocyanate (1.3 g, 7.65 mmol) and dicyclohexylcarbodiimide (1.11 g, 5.4 mmol) were added. After 4 hours, the reaction was cooled, diluted with an equal volume of ether, and filtered. The filter cake was washed with additional ether and the collected solids dried in vacuo to provide 0.94 g of (R)-benzyl 1-(6-(3-chlorophenylamino)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-yl)ethylcarbamate: ESMS MH+=429.

Workup

  1. temperaturethe reaction was cooled
  2. filtrationfiltered
  3. washThe filter cake was washed with additional ether
  4. customthe collected solids dried in vacuo

Sources & evidence

ORD record
ord-99b478e2c89843c2a1f93812d9885667
Source dataset
uspto-grants-2013_07
Patent number
US08481538B2

Linked notes

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