Benzenesulfonyl chloride → HCID 58869108, compound

HRID 1623114Notes

Reaction equation

HRID 1623114 reaction equation
ClC1C=C(C=CC=1)C(OO)=O.[CH3:12][O:13][N:14]([CH2:18][CH2:19][CH2:20][CH2:21][N:22]1[C:34]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N:27]=[CH:26][C:25]=2[N:24]=[C:23]1[CH2:35][CH2:36][CH3:37])[C:15](=[O:17])[CH3:16].[OH-].[NH4+:39].C1(S(Cl)(=O)=O)C=CC=CC=1.[OH-].[Na+]>ClCCl.C(=O)(O)[O-].[Na+]>[NH2:39][C:26]1[C:25]2[N:24]=[C:23]([CH2:35][CH2:36][CH3:37])[N:22]([CH2:21][CH2:20][CH2:19][CH2:18][N:14]([O:13][CH3:12])[C:15](=[O:17])[CH3:16])[C:34]=2[C:33]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[N:27]=1

Participants

8

Reactant 5

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 86612247HCID 86612247, compound

Product 1

HCID 58869108HCID 58869108, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

3-Chloroperoxybenzoic acid (77% pure, 0.44 g, 1.95 mmol) (mCPBA) was added to a solution of N-methoxy-N-[4(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]acetamide (1.0 mmol) in dichloromethane (25 mL) cooled to 0° C. and stirred for 10 minutes, and then the reaction was stirred for one hour at ambient temperature. Concentrated ammonium hydroxide (10 mL) and phenylsulfonyl chloride (0.22 mL, 1.75 mmol) were sequentially added and the reaction mixture was stirred for 1 hour and then diluted with dichloromethane (50 mL) and saturated aqueous sodium bicarbonate solution (2×50 mL) containing 5% sodium hydroxide (5 mL). The layers were separated and the aqueous layer was extracted with dichloromethane (2×25 mL) and the combined organic solutions were dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide a brown oil. The material was purified by flash column chromatography on silica gel (eluting with 5% methanol and concentrated ammonium hydroxide (2 mL) in dichloromethane). The resulting crystalline solid was recrystallized twice from acetonitrile and water and dried overnight under vacuum at 70° C. to afford 0.26 g of N-[4-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N-methoxyacetamide as light yellow needles, mp 138-140° C. MS (APCI) m/z 370 (M+H+); Anal. calcd for C20H27N5O2: C, 65.02; H, 7.37; N, 18.96. Found: C, 64.97; H, 7.04; N, 18.80.

Workup

  1. stirringthe reaction was stirred for one hour at ambient temperature
  2. stirringthe reaction mixture was stirred for 1 hour
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane (2×25 mL)
  5. dry with materialthe combined organic solutions were dried over potassium carbonate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto provide a brown oil
  9. customThe material was purified by flash column chromatography on silica gel (eluting with 5% methanol and concentrated ammonium hydroxide (2 mL) in dichloromethane)
  10. customThe resulting crystalline solid was recrystallized twice from acetonitrile and water
  11. customdried overnight under vacuum at 70° C.

Sources & evidence

ORD record
ord-a50f076ddf7043c4880fc805a01a65ea
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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