Dichloromethane → N-{4-[8-(chloromethyl)-5,6-dimethyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl]butyl}-N'-cyclohexylurea

HRID 599416Notes

Reaction equation

HRID 599416 reaction equation
[CH:1]1([N:7]=[C:8]=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[Cl:11][CH2:12][C:13]1[N:14]([CH2:27][CH2:28][CH2:29][CH2:30][NH2:31])[C:15]2[C:20]([CH3:21])=[C:19]([CH3:22])[N:18]3[N:23]=[N:24][N:25]=[C:17]3[C:16]=2[N:26]=1.ClCCl>C(N(CC)CC)C>[Cl:11][CH2:12][C:13]1[N:14]([CH2:27][CH2:28][CH2:29][CH2:30][NH:31][C:8]([NH:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:9])[C:15]2[C:20]([CH3:21])=[C:19]([CH3:22])[N:18]3[N:23]=[N:24][N:25]=[C:17]3[C:16]=2[N:26]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 18502Cyclohexyl isocyanate2×HCID 67052345HCID 67052345, compound

Product 1

HCID 67052393N-{4-[8-(chloromethyl)-5,6-dimethyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl]butyl}-N'-cyclohexylureaYield 90.6%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent2×

Procedure

Cyclohexyl isocyanate (0.285 mL, 2.20 mmol) was added to a flask containing 4-[8-(chloromethyl)-5,6-dimethyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl]butan-1-amine hydrochloride (680 mg, 1.98 mmol), triethylamine (0.311 mL, 2.2 mmol), and dichloromethane (20 mL). The reaction mixture was stirred at room temperature for 2 hours and additional triethylamine and cyclohexyl isocyanate (1.1 equivalents each) were added. The reaction mixture was stirred overnight at room temperature, then was partitioned between dichloromethane (50 mL) and 2:1 water/saturated aqueous sodium carbonate (30 mL). The aqueous layer was extracted with dichloromethane (3×20 mL). The organic layers were combined, washed with 0.5 M aqueous sodium hydroxide (2×30 mL), and concentrated under reduced pressure. The resulting white solid was triturated with ethyl acetate, isolated by filtration, and washed with ethyl acetate and water to provide 777 mg of N-{4-[8-(chloromethyl)-5,6-dimethyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl]butyl}-N′-cyclohexylurea.

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. customwas partitioned between dichloromethane (50 mL) and 2:1 water/saturated aqueous sodium carbonate (30 mL)
  3. extractionThe aqueous layer was extracted with dichloromethane (3×20 mL)
  4. washwashed with 0.5 M aqueous sodium hydroxide (2×30 mL)
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting white solid was triturated with ethyl acetate
  7. customisolated by filtration
  8. washwashed with ethyl acetate and water

Sources & evidence

ORD record
ord-0195a4ef4016429f9d0412efd0822af6
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

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