4-(4-Bromobenzyl)morpholine → 4-(Morpholinomethyl)aniline

HRID 1889824Notes

Reaction equation

HRID 1889824 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[N:16]3[N:17]=[C:18]([NH2:20])[N:19]=[C:15]3[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].Br[C:22]1[CH:34]=[CH:33][C:25]([CH2:26][N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[CH:24][CH:23]=1>>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[N:16]3[N:17]=[C:18]([NH:20][C:22]4[CH:23]=[CH:24][C:25]([CH2:26][N:27]5[CH2:32][CH2:31][O:30][CH2:29][CH2:28]5)=[CH:33][CH:34]=4)[N:19]=[C:15]3[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])=[O:4].[N:27]1([CH2:26][C:25]2[CH:33]=[CH:34][C:22]([NH2:16])=[CH:23][CH:24]=2)[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 7835034-(4-Bromobenzyl)morpholineHCID 591864375-(3-(Methylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 2

HCID 7768514-(Morpholinomethyl)anilineYield 285.5%HCID 59186221HCID 59186221, compound

Procedure

[5-(3-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(4-morpholin-4-ylmethyl-phenyl)-amine was prepared from 5-(3-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (125 mg, 0.43 mmol) and 4-(4-bromobenzyl)morpholine (122 mg, 0.48 mmol) in a manner analogous to Example 77 to yield 5-(3-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(4-morpholin-4-ylmethyl-phenyl)-amine (118 mg, 59%) as an off-white powder following purification on a 4 g Isco silica gel column using methanol in dichloromethane (0-20%) as eluent. MP=210-211° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.64 (s, 1H), 8.78 (s, 1H), 8.36 (d, J=7.50 Hz, 1H), 8.11 (d, J=7.50, 1H), 7.89 (t, J=15.0 Hz, 7.50 Hz, 1H), 7.70 (m, 1H), 7.63 (m, 3H), 7.35 (d, J=7.50 Hz, 1H), 7.18 (d, J=9.6 Hz, 2H) 3.55 (m, 4H), 3.40-3.28 (m, 5H), 2.32 (m, 4H). MS=464 (MH)+.

Sources & evidence

ORD record
ord-606a69be8b9848d6b997d36c0a71c8a5
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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