Ethyl isocyanate → HCID 10428215, compound

HRID 2252336Notes

Reaction equation

HRID 2252336 reaction equation
[CH:1]([C:4]1[N:8]2[CH:9]=[C:10]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH2:20][OH:21])[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1)([CH3:3])[CH3:2].[CH2:22]([N:24]=[C:25]=[O:26])[CH3:23]>>[CH:1]([C:4]1[N:8]2[CH:9]=[C:10]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH2:20][O:21][C:25](=[O:26])[NH:24][CH2:22][CH3:23])[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 8022Ethyl isocyanateHCID 17974489HCID 17974489, compound

Product 1

HCID 10428215HCID 10428215, compoundYield 48%

Conditions

Temperature
60 °C

Procedure

A suspension of [2-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-phenyl]-methanol (28 mg, 0.1 mmol) and ethyl isocyanate (14 μL, 0.2 mmol) was heated at 60° C. for 18 hours. The reaction was then cooled and concentrated in vacuo to an oil. The crude was purified by flash chromatography (eluting with 2% methanol/ethyl acetate), followed by suspension in 7:3 hexane:ethyl acetate. The solid was filtered to give the title compound as a white solid (17 mg, 48%) LCMS (m/z) 355.4 (M+1).

Workup

  1. temperatureThe reaction was then cooled
  2. concentrationconcentrated in vacuo to an oil
  3. customThe crude was purified by flash chromatography (eluting with 2% methanol/ethyl acetate)
  4. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-c99599e702b741588460f071bd505122
Source dataset
uspto-grants-2008_01
Patent number
US07321040B2

Reaction notes

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