Tert-butyl(2-(2-chloroethoxy)ethoxy)dimethylsilane → 2-(4-(2-(2-(Tert-butyldimethylsilyloxy)ethoxy)ethoxy)-2-methylphenethyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine

HRID 340362Notes

Reaction equation

HRID 340362 reaction equation
[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][C:8]([CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=3[CH3:21])=[CH:7][C:6]=2[C:5]2[CH:22]=[CH:23][C:24]([CH3:26])=[CH:25][C:4]=2[N:3]=1.[C:27]([Si:31]([O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39]Cl)([CH3:33])[CH3:32])([CH3:30])([CH3:29])[CH3:28]>>[Si:31]([O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][CH2:12][C:8]2[CH:9]=[N:10][C:11]3[C:6]([CH:7]=2)=[C:5]2[CH:22]=[CH:23][C:24]([CH3:26])=[CH:25][C:4]2=[N:3][C:2]=3[NH2:1])=[C:15]([CH3:21])[CH:16]=1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:33])[CH3:32]

Participants

3

Reactant 2

HCID 4555750Tert-butyl(2-(2-chloroethoxy)ethoxy)dimethylsilaneHCID 581665094-(2-(5-Amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenol

Product 1

HCID 668751932-(4-(2-(2-(Tert-butyldimethylsilyloxy)ethoxy)ethoxy)-2-methylphenethyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine

Procedure

2-(4-(2-(2-(Tert-butyldimethylsilyloxy)ethoxy)ethoxy)-2-methylphenethyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine was prepared following an analogous procedure to the preparation described for Example 145/Step 1, but using 4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenol (from Example 50) with tert-butyl(2-(2-chloroethoxy)ethoxy)dimethylsilane.

Sources & evidence

ORD record
ord-f2eb2d3eb06d43358278a710dd3e9ca7
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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