Chloroform → N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}methanesulfonamide

HRID 2121670Notes

Reaction equation

HRID 2121670 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:19]2[C:18]([CH3:20])=[CH:17][N:16]=[C:15]([NH2:21])[C:14]=2[N:13]=[C:12]1[CH2:22][O:23][CH2:24][CH3:25].C(N(CC)CC)C.C(Cl)(Cl)Cl>[OH-].[Na+]>[NH2:21][C:15]1[C:14]2[N:13]=[C:12]([CH2:22][O:23][CH2:24][CH3:25])[N:11]([CH2:10][CH2:9][CH2:8][CH2:7][NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[C:19]=2[C:18]([CH3:20])=[CH:17][N:16]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 219460261-(4-aminobutyl)-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-4-amine

Product 1

HCID 10286886N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}methanesulfonamide

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Methanesulfonyl chloride (4 eq) was added dropwise to a mixture of 1-(4-aminobutyl)-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-4-amine (2.25 g, 8.11 mmol), triethylamine (10.2 mL, 73.0 mmol) and chloroform (225 mL). The solvent was removed under reduced pressure to provide an oil. The oil was dissolved in 10% sodium hydroxide (200 mL) then extracted with chloroform (3×300 mL). The combined extracts were dried over magnesium sulfate and then concentrated under reduced pressure to provide a clear oil. The oil was purified by column chromatography (silica gel eluting with 90/10 dichloromethane/methanol) to provide a white solid. This material was dried overnight under vacuum at 80° C. to provide 0.71 g of N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}methanesulfonamide as a white solid, m.p. 173-175° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto provide an oil
  3. extractionthen extracted with chloroform (3×300 mL)
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto provide a clear oil
  7. customThe oil was purified by column chromatography (silica gel eluting with 90/10 dichloromethane/methanol)
  8. customto provide a white solid
  9. customThis material was dried overnight under vacuum at 80° C.

Sources & evidence

ORD record
ord-7982ddae964046568367c9628aa04570
Source dataset
uspto-grants-2004_02
Patent number
US06696465B2

Reaction notes

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