Ethyl isocyanate → 1-(4,6-Dibromothiazolo[5,4-c]pyridin-2-yl)-3-ethylurea

HRID 712177Notes

Reaction equation

HRID 712177 reaction equation
[Br:1][C:2]1[C:7]2[S:8][C:9]([NH2:11])=[N:10][C:6]=2[CH:5]=[C:4]([Br:12])[N:3]=1.[CH2:13]([N:15]=[C:16]=[O:17])[CH3:14]>O1CCOCC1.O>[Br:1][C:2]1[C:7]2[S:8][C:9]([NH:11][C:16]([NH:15][CH2:13][CH3:14])=[O:17])=[N:10][C:6]=2[CH:5]=[C:4]([Br:12])[N:3]=1

Participants

5

Reactant 2

HCID 8022Ethyl isocyanateHCID 580332294,6-Dibromothiazolo[5,4-c]pyridin-2-amine

Product 1

HCID 580332371-(4,6-Dibromothiazolo[5,4-c]pyridin-2-yl)-3-ethylureaYield 82.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4,6-dibromothiazolo[5,4-c]pyridin-2-amine (1.47 g, 56.74% as per LCMS, 2.70 mmol) in 1,4-dioxane (75 mL) was added ethylisocyanate (1.30 mL, 16.25 mmol) and the resulting reaction mixture was heated to 80° C. for 16 h. The solvent was distilled off under reduced pressure and the residue was then co-distilled with hexane (twice). The solid thus obtained was stirred in hot water at 80° C. for 30 min then filtered. The solid material was purified over silica gel (100-200 M, 30-40% EtOAc-hexane) to obtain the desired product as an off-white solid (0.85 g, 82%).

Workup

  1. customthe resulting reaction mixture
  2. distillationThe solvent was distilled off under reduced pressure
  3. customThe solid thus obtained
  4. filtrationthen filtered
  5. customThe solid material was purified over silica gel (100-200 M, 30-40% EtOAc-hexane)

Sources & evidence

ORD record
ord-811152d98b6e43118e5c05aae97a55bc
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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