tert-butyl N-(6-iodohexyl)carbamate → tert-butyl 6-{[2-(ethoxymethyl)-1-(2-{[(isopropylamino)carbonyl]amino}-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}hexylcarbamate

HRID 540877Notes

Reaction equation

HRID 540877 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:19][C:20]([NH:23][C:24]([NH:26][CH:27]([CH3:29])[CH3:28])=[O:25])([CH3:22])[CH3:21])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([OH:17])=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:18]=1)[CH3:2].I[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41]>>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:19][C:20]([NH:23][C:24]([NH:26][CH:27]([CH3:28])[CH3:29])=[O:25])([CH3:22])[CH3:21])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([O:17][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:18]=1)[CH3:2]

Participants

3

Reactant 2

HCID 10616156tert-butyl N-(6-iodohexyl)carbamateHCID 136347849N-{2-[2-(ethoxymethyl)-7-hydroxy-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}-N'-isopropylurea

Product 1

HCID 68972024tert-butyl 6-{[2-(ethoxymethyl)-1-(2-{[(isopropylamino)carbonyl]amino}-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}hexylcarbamateYield 92.3%

Procedure

Following the method described in Part L of Example 2, N-{2-[2-(ethoxymethyl)-7-hydroxy-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}-N′-isopropylurea (3.12 g, 7.80 mmol) was treated with tert-butyl 6-iodohexylcarbamate (2.81 g, 8.58 mmol) to afford 4.31 g of tert-butyl 6-{[2-(ethoxymethyl)-1-(2-{[(isopropylamino)carbonyl]amino}-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}hexylcarbamate. The material was used without purification in the next step.

Sources & evidence

ORD record
ord-5c465e7abd5343949a9dff11c2556de1
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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