Triethylamine → HCID 58970687, compound

HRID 598043Notes

Reaction equation

HRID 598043 reaction equation
C(N(CC)CC)C.Cl.Cl.[NH2:10][C:11]([CH3:33])([CH3:32])[CH2:12][N:13]1[C:25]2[C:24]3[N:23]=[CH:22][C:21]([Br:26])=[CH:20][C:19]=3[N:18]=[C:17]([NH2:27])[C:16]=2[N:15]=[C:14]1[CH2:28][O:29][CH2:30][CH3:31].[CH3:34][S:35](Cl)(=[O:37])=[O:36]>ClCCl>[NH2:27][C:17]1[C:16]2[N:15]=[C:14]([CH2:28][O:29][CH2:30][CH3:31])[N:13]([CH2:12][C:11]([NH:10][S:35]([CH3:34])(=[O:37])=[O:36])([CH3:32])[CH3:33])[C:25]=2[C:24]2[N:23]=[CH:22][C:21]([Br:26])=[CH:20][C:19]=2[N:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67052467HCID 67052467, compound

Product 1

HCID 58970687HCID 58970687, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
4 °C

Procedure

Triethylamine (13.02 g, 128.7 mmol) was added to a suspension of 1-(2-amino-2-methylpropyl)-7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine dihydrochloride (6.00 g, 12.9 mmol) in dichloromethane (500 mL), and the reaction was cooled to 4° C. A solution of methanesulfonyl chloride (1.62 g, 14.2 mmol) in dichloromethane (10 mL) was then added dropwise. The reaction mixture was allowed to warm to room temperature, stirred for 24 hours, diluted with dichloromethane (200 mL), washed sequentially with water (200 mL), 4% aqueous sodium carbonate (2×200 mL), water (200 mL), and brine (200 mL), and concentrated under reduced pressure. The crude product was purified by automated flash chromatography (FLASH 40+M silica cartridge, eluting with 0 to 25% CMA in chloroform) followed by recrystallization from acetonitrile to provide 5.21 g of N-{2-[4-amino-7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-1,1-dimethylethyl}methanesulfonamide as a white solid, 211-212° C.

Workup

  1. temperatureto warm to room temperature
  2. washwashed sequentially with water (200 mL), 4% aqueous sodium carbonate (2×200 mL), water (200 mL), and brine (200 mL)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by automated flash chromatography (FLASH 40+M silica cartridge, eluting with 0 to 25% CMA in chloroform)
  5. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-d640c6207a2e40ac80b55b81bc506394
Source dataset
uspto-grants-2011_03
Patent number
US07897609B2

Reaction notes

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