4-Toluenesulfonyl chloride → HCID 59026673, compound

HRID 606135Notes

Reaction equation

HRID 606135 reaction equation
[CH2:1]([C:4]1[N:5]([CH2:17][C:18]2[CH:22]=[C:21]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[O:20][N:19]=2)[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1)[CH2:2][CH3:3].C1C=C(Cl)C=C(C(OO)=O)C=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH-].[NH4+:52]>>[CH2:1]([C:4]1[N:5]([CH2:17][C:18]2[CH:22]=[C:21]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[O:20][N:19]=2)[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[C:8]([NH2:52])[C:7]=2[N:16]=1)[CH2:2][CH3:3]

Participants

5

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 67041319HCID 67041319, compound

Product 1

HCID 59026673HCID 59026673, compound

Procedure

The methods described in Part I of Example 35 were used to treat 2-propyl-1-[(5-pyridin-3-ylisoxazol-3-yl)methyl]-1H-imidazo[4,5-c]quinoline (0.920 g, 3.00 mmol) with mCPBA (0.808 g of 77% pure material, 3.6 mmol) followed by p-toluenesulfonyl chloride (0.629 g, 3.30 mmol) and concentrated ammonium hydroxide (15 mL) and purify the final product to provide 0.46 g of 2-propyl-1-[(5-pyridin-3-ylisoxazol-3-yl)methyl]-1H-imidazo[4,5-c]quinolin-4-amine as a tan crystalline solid, mp 206-207° C.

Workup

  1. custompurify the final product

Sources & evidence

ORD record
ord-c2dceeada19f4751b84a3406908a2c9b
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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