Morpholine → HCID 59506517, compound

HRID 1798896Notes

Reaction equation

[CH2:1]([N:8]1[C:18]2=[C:19]3[C:14](=[N:15][C:16](S(C)(=O)=O)=[N:17]2)[N:13]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[CH2:12][CH2:11][C:10]3=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>CS(C)=O.CCN(C(C)C)C(C)C>[CH2:1]([N:8]1[C:18]2=[C:19]3[C:14](=[N:15][C:16]([N:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)=[N:17]2)[N:13]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[CH2:12][CH2:11][C:10]3=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

The mixture of 1-benzyl-5-(4-methoxybenzyl)-7-(methylsulfonyl)-1,3,4,5-tetrahydro-1,2,5,6,8-pentaazaacenaphthylene (0.1 mmol) and morpholine (0.2 mmol) in anhydrous DMSO (1 mL) and DIPEA (0.06 mL) was heated at 100° C. for 64 h in 2-dram vials. The solvent was then removed on Genevac. The residue was re-brought up to DMSO (1.2 mL) and was purified by HPLC using reverse phase column chromatography with a Maccel AQ C18 column and a gradient of 1-95% ACN/water containing 0.05% trifluoroacetic acid , to yield the 4-(1-benzyl-5-(4-methoxybenzyl)-1,3,4,5-tetrahydro-1,2,5,6,8-pentaazaacenaphthylen-7-yl)morpholine compound 131 White solid, 50% yiled, M.p. 118-120° C.; 1H NMR (CDCl3, 400 MHz) δ 7.33-7.23 (m, 7H), 6.86 (d, J=8.4 Hz, 2H), 5.33 (brs, 2H), 4.71 (s, 2H), 3.92 (m, 4H), 3.79 (m, 7H), 3.48 (m, 2H), 2.98 (t, J=6.4 Hz, 2H). LC-Mass (m/e): 457.56 (M+1).

Workup

customThe solvent was then removed on Genevac
customwas purified by HPLC

Sources & evidence

ORD record: ord-391cb164f33c496f9c11649da5f06f45
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343983B2

Reaction notes

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