Bromocyclopentane → 2-(4-(Cyclopentyloxy)phenethyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine

HRID 340353Notes

Reaction equation

HRID 340353 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][CH:15]=3)=[CH:7][C:6]=2[C:5]2[CH:21]=[CH:22][C:23]([CH3:25])=[CH:24][C:4]=2[N:3]=1.Br[CH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>>[CH:27]1([O:20][C:17]2[CH:16]=[CH:15][C:14]([CH2:13][CH2:12][C:8]3[CH:9]=[N:10][C:11]4[C:6]([CH:7]=3)=[C:5]3[CH:21]=[CH:22][C:23]([CH3:25])=[CH:24][C:4]3=[N:3][C:2]=4[NH2:1])=[CH:19][CH:18]=2)[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

3

Reactant 2

HCID 8728BromocyclopentaneHCID 582135504-(2-(5-Amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)phenol

Product 1

HCID 582136052-(4-(Cyclopentyloxy)phenethyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine

Procedure

2-(4-(Cyclopentyloxy)phenethyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine was prepared from 4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)phenol (from Example 170) following the procedure described for Example 136, but using bromocyclopentane. 1H NMR (Acetone-d6): δ 8.75 (d, 2H), 8.30 (d, 1H), 7.45 (s, 1H), 7.20 (d, 1H), 7.14 (d, 2H), 6.79 (d, 2H), 4.73-4.81 (m, 1H), 3.22 (t, 2H), 3.05 (t, 2H), 2.47 (s, 3H), 1.85-1.96 (m, 2H), 1.70-1.79 (m, 4H), 1.56-1.64 (m, 2H). LRMS [M+H]=398.2

Sources & evidence

ORD record
ord-2042f6f9045d4f1b83c90bc3cda1f076
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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