Hydrochloric Acid → HCID 69506691, compound

HRID 2366639Notes

Reaction equation

HRID 2366639 reaction equation
[CH2:1]([C:4]1[N:5]([CH2:17][CH2:18][C:19]([NH2:21])=[O:20])[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:28])C=C(C(OO)=O)C=1.[OH-].[NH4+:34].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.Cl>CO.C(OCC)C>[ClH:28].[NH2:34][C:8]1[C:7]2[N:16]=[C:4]([CH2:1][CH2:2][CH3:3])[N:5]([CH2:17][CH2:18][C:19]([NH2:21])=[O:20])[C:6]=2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 57447040HCID 57447040, compound

Product 1

HCID 69506691HCID 69506691, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

3-(2-Propyl-1H-imidazo[4,5-c]quinolin-1-yl)propanamide (3.9 g, 14 mmol) was treated with mCPBA (6.19 g, 26.9 mmol) followed by ammonium hydroxide (50 mL) and p-toluenesulfonyl chloride (4.6 g, 24 mmol) according to the method described in Part D of Example 8. The crude product was dissolved in methanol, and hydrogen chloride (1.25 mL of a 1 M solution in diethyl ether) was added. The resulting solid was isolated by filtration and dried overnight under high vacuum to provide 0.477 g of 3-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)propanamide hydrochloride as tan needles, mp 242-243° C.

Workup

  1. customThe resulting solid was isolated by filtration
  2. customdried overnight under high vacuum

Sources & evidence

ORD record
ord-1b300ce76ce8410a856bf9c4ae2f6bd8
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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