4-Toluenesulfonyl chloride → HCID 57447015, compound

HRID 2366596Notes

Reaction equation

HRID 2366596 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][CH2:20][C:21]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[O:22])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2].C1C=C(Cl)C=C(C(OO)=O)C=1.[OH-].[NH4+:41].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>ClCCl>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][CH2:20][C:21]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[O:22])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:41])[C:8]=2[N:17]=1)[CH3:2]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acid2×HCID 57447014HCID 57447014, compound

Product 1

HCID 57447015HCID 57447015, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(Ethoxymethyl)-1-(4-morpholin-4-yl-4-oxobutyl)-1H-imidazo[4,5-c]quinoline (6.9 g, 18 mmol) was treated with mCPBA (7.9 g, 35 mmol), concentrated ammonium hydroxide (50 mL of 29%), and p-toluenesulfonyl chloride (6.0 g, 32 mmol) according to a modification of the method described in Part E of Example 3. The mCPBA addition was carried out at 0° C., and the reaction was carried out in dichloromethane (150 mL). The crude product was triturated with 2:1 ethyl acetate:hexane (15 mL), and the resulting solid was isolated by filtration, washed with 30:70 ethyl acetate:hexane, recrystallized twice from methanol:water, and dried overnight in a vacuum oven at 70° C. to provide 2-(ethoxymethyl)-1-(4-morpholin-4-yl-4-oxobutyl)-1H-imidazo[4,5-c]quinolin-4-amine as yellow crystals, mp 201-203° C.

Workup

  1. customwas carried out at 0° C.
  2. customThe crude product was triturated with 2:1 ethyl acetate
  3. customhexane (15 mL), and the resulting solid was isolated by filtration
  4. washwashed with 30:70 ethyl acetate
  5. customhexane, recrystallized twice from methanol
  6. dry with materialwater, and dried overnight in a vacuum oven at 70° C.

Sources & evidence

ORD record
ord-7407809c529b4cceab86f73dee055e86
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

Loading…