4-(4-Bromobenzyl)morpholine → HCID 67481528, compound

HRID 1889773Notes

Reaction equation

HRID 1889773 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]3[N:13]([N:17]=[C:18]([NH2:20])[N:19]=3)[CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=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.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]3[N:13]([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]=3)[CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

4

Reactant 3

HCID 7835034-(4-Bromobenzyl)morpholineHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 575023768-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

Product 1

HCID 67481528HCID 67481528, compound

Procedure

[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(4-morpholin-4-ylmethyl-phenyl)-amine was prepared from 8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (50.0 mg, 0.173 mmol) and 4-(4-bromo-benzyl)-morpholine (55.0 mg, 0.215 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (20.0 mg, 0.0366 mmol) as the ligand in a manner analogous to Step 2d and was isolated as a yellow foam (0.006 g, 7%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.50 (d, J=6.6 Hz, 1H), 8.23 (d, J=8.3 Hz, 2H), 8.09 (d, J=8.3 Hz, 2H), 7.66 (d, J=7.4 Hz, 1H), 7.55 (d, J=8.4 Hz, 2H), 7.32 (d, J=8.2 Hz, 2H), 7.03 (t, J=6.7 Hz, 1H), 6.86 (s, 1H), 3.74-3.69 (m, 4H), 3.48 (s, 2H), 3.11 (s, 3H), 2.48-2.43 (m, 4H). MS=464 (MH)+.

Sources & evidence

ORD record
ord-35458c9d4486412b827c18eeb857aeb4
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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