Propargyl bromide → HCID 22254454, compound

HRID 434012Notes

Reaction equation

[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH3:18])[N:14]([CH2:15][CH2:16][OH:17])[C:10]=2[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.[CH2:19](Br)[C:20]#[CH:21]>>[CH3:18][C:13]1[N:14]([CH2:15][CH2:16][O:17][CH2:21][C:20]#[CH:19])[C:10]2[C:9]3[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=1

Participants

Reactant 2

HCID 7842Propargyl bromide

HCID 22254483HCID 22254483, compound

Product 1

HCID 22254454HCID 22254454, compoundYield 47.7%

Procedure

Using the general method of Example 1 Part A, 2-(4-amino-2-methyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)ethanol (0.763 g, 3.098 mmol) was reacted with propargyl bromide (80% in toluene, 1.1 mL, 9.29 mmol) to provide 0.42 g of 2-methyl-1-[2-(prop-2-ynyloxy)ethyl]-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine as a brown oil.

Sources & evidence

ORD record: ord-12b805cb778746b193c40cb2fb2f9b38
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06670372B2

Reaction notes

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