Chlorosuccinimide → HCID 11483894, compound

HRID 229362Notes

Reaction equation

HRID 229362 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[N:8]=[C:9]2[CH:14]=[C:13]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[CH:12]=[CH:11][N:10]2[CH:21]=1)=[O:5])[CH3:2].[Cl:22]N1C(=O)CCC1=O>O1CCCC1>[Cl:22][C:21]1[N:10]2[CH:11]=[CH:12][C:13]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)=[CH:14][C:9]2=[N:8][C:7]=1[NH:6][C:4]([NH:3][CH2:1][CH3:2])=[O:5]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 11150214HCID 11150214, compound

Product 1

HCID 11483894HCID 11483894, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl-3-(7-pyridin-3-yl-imidazo[1,2-a]pyridin-2-yl)-urea (1) (196 mg, 0.70 mmol), prepared as in Example 1, was dissolved/suspended in tetrahydrofuran (80 mL) and cooled to 0° C., (ice/water). N-chlorosuccinimide (102 mg, 0.77 mmol) was added and the mixture stirred at 0° C. for 2 h. All solids had dissolved and the reaction was complete by LCMS after this time. The solvent was removed under reduced pressure to give a residue which was purified by chromatography on silica gel (2% methanol/dichloromethane), followed by recrystallization from ethyl acetate/methanol to afford 1-(3-chloro-7-pyridin-3-yl-imidazo[1,2-a]pyridin-2-yl)-3-ethyl-urea (2) as a solid (132 mg). HRMS (EI+) calcd C15H1435ClN5O (M+) 315.0887, found 315.0882; calcd C15H1437ClN5O (M+) 317.0857, found 317.0862.

Workup

  1. dissolutionAll solids had dissolved
  2. customThe solvent was removed under reduced pressure
  3. customto give a residue which
  4. customwas purified by chromatography on silica gel (2% methanol/dichloromethane)
  5. customfollowed by recrystallization from ethyl acetate/methanol

Sources & evidence

ORD record
ord-4aa609f20d0f4c38bfee683c9801fa50
Source dataset
uspto-grants-2009_07
Patent number
US07563788B2

Reaction notes

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