Ethyl isocyanate → HCID 66628276, compound

HRID 2200980Notes

Reaction equation

HRID 2200980 reaction equation
[NH2:1][C:2]1[N:31]=[C:5]2[N:6]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[C:7]([CH3:20])=[C:8]([C:18]#[N:19])[C@@H:9]([C:10]3[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=3)[N:4]2[N:3]=1.S([O-])([O-])(=O)=O.[Na+].[Na+].[CH2:39]([N:41]=[C:42]=[O:43])[CH3:40]>N1C=CC=CC=1>[C:18]([C:8]1[C@@H:9]([C:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=2)[N:4]2[N:3]=[C:2]([NH:1][C:42]([NH:41][CH2:39][CH3:40])=[O:43])[N:31]=[C:5]2[N:6]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:30])[F:29])[CH:22]=2)[C:7]=1[CH3:20])#[N:19]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 24436Sodium SulfateHCID 66627900HCID 66627900, compound

Product 1

HCID 66628276HCID 66628276, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

Under an atmosphere of argon protective gas, (7R)-2-amino-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile (15 mg, 33 μmol) was dissolved in abs. pyridine (2 ml), and solid sodium sulfate (spatula tip) and ethyl isocyanate (46.6 mg, 655 μmol, 20 eq.) were added. The reaction mixture was then heated in a microwave reactor (2.5 h at 100° C., then 2 h at 110° C. and finally 2 h at 125° C.). After cooling, the reaction mixture was filtered, the filtrate was concentrated under reduced pressure and the residue was purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (7.8 mg, 48% of theory).

Workup

  1. custom2 h
  2. customat 110° C.
  3. customfinally 2 h
  4. customat 125° C.
  5. temperatureAfter cooling
  6. filtrationthe reaction mixture was filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA)
  9. customAfter lyophilization, the product was obtained as a solid (7.8 mg, 48% of theory)

Sources & evidence

ORD record
ord-051700be43bf41c3ad5d8417636cebe4
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

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