Thionyl Chloride → HCID 67041486, compound

HRID 606140Notes

Reaction equation

HRID 606140 reaction equation
S(Cl)([Cl:3])=O.[NH2:5][C:6]1[C:15]2[N:16]=[C:17]([CH2:32]O)[N:18]([CH2:19][C:20]3[O:24][N:23]=[C:22]([C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)[CH:21]=3)[C:14]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1>ClCCl>[ClH:3].[Cl:3][CH2:32][C:17]1[N:18]([CH2:19][C:20]2[O:24][N:23]=[C:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH:21]=2)[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6]([NH2:5])[C:15]=2[N:16]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 59026688HCID 59026688, compound

Product 1

HCID 67041486HCID 67041486, compoundYield 112.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The methods described in Examples 30 and 31 were repeated on a larger scale to provide (4-amino-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c]quinolin-2-yl)methanol. The reaction described in Example 31 was heated at reflux and was complete within three hours. Thionyl chloride (0.45 mL, 6.17 mmol) was added dropwise to a suspension of (4-amino-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c]quinolin-2-yl)methanol (1.2 g, 3.08 mmol) in dichloromethane (30 mL), and the mixture was stirred at room temperature for 1.8 hours. The volatiles were removed under reduced pressure, and the residue was combined with material from another run, triturated with a mixture of ethanol and diethyl ether, and isolated by filtration to provide 1.54 g 2-(chloromethyl)-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c]quinolin-4-amine hydrochloride.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customThe volatiles were removed under reduced pressure
  4. customtriturated with a mixture of ethanol and diethyl ether
  5. customisolated by filtration

Sources & evidence

ORD record
ord-33b7940117ac48718cf4067534983f18
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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