4-Toluenesulfonyl chloride → HCID 57447054, compound

HRID 2366661Notes

Reaction equation

HRID 2366661 reaction equation
[CH3:1][NH:2][C:3](=[O:31])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:27]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:20]=[CH:19][C:18]=2[N:17]=[C:16]1[CH2:28][CH2:29][CH3:30].C1C=C(Cl)C=C(C(OO)=O)C=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH-].[NH4+:55]>>[NH2:55][C:19]1[C:18]2[N:17]=[C:16]([CH2:28][CH2:29][CH3:30])[N:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([NH:2][CH3:1])=[O:31])[C:27]=2[C:26]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N:20]=1

Participants

5

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 69506817HCID 69506817, compound

Product 1

HCID 57447054HCID 57447054, compound

Procedure

N-Methyl-12-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)dodecanamide (3.8 g, 9.0 mmol) was treated with mCPBA (4.65 g, 26.9 mmol) followed by ammonium hydroxide (40 mL) and p-toluenesulfonyl chloride (2.31 g, 12.1 mmol) according to the method described in Part D of Example 8. The crude product was purified as described in Part D of Example 8 to provide 1.036 g of 12-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-N-methyldodecanamide as a brown crystalline solid, mp 135-137° C.

Workup

  1. customThe crude product was purified

Sources & evidence

ORD record
ord-1a39cfc158984c8e99a18198c333116f
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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