4-(3-bromobenzyl)morpholine → HCID 59612382, compound

HRID 1889776Notes

Reaction equation

HRID 1889776 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:23]=[C:24]([CH:32]=[CH:33][CH:34]=1)[CH2:25][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]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:33]4[CH:34]=[CH:22][CH:23]=[C:24]([CH2:25][N:26]5[CH2:31][CH2:30][O:29][CH2:28][CH2:27]5)[CH:32]=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 7830824-(3-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 59612382HCID 59612382, compound

Procedure

[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(3-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-(3-bromo-benzyl)-morpholine (54.0 mg, 0.211 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 an orange foam (0.021 g, 26%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.51 (d, J=6.5 Hz, 1H), 8.24 (d, J=7.4 Hz, 2H), 8.09 (d, J=7.3 Hz, 2H), 7.66 (d, J=7.0 Hz, 1H), 7.58 (d, J=8.0 Hz, 1H), 7.49 (s, 1H), 7.35-7.29 (m, 1H), 7.05-6.97 (m, 2H), 6.87 (s, 1H), 3.75-3.70 (m, 4H), 3.54 (s, 2H), 3.11 (s, 3H), 2.52-2.45 (m, 4H). MS=464 (MH)+.

Sources & evidence

ORD record
ord-e3154ccc50b74adcae410f75e928fabd
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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