Sodium Carbonate → HCID 70662762, compound

HRID 2370055Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[C:9]2[NH:14][C:13](=[O:15])[C:12](=[CH:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20]C=3)[NH:11][C:10]2=[O:24])=[N:6][CH:7]=1.Br[CH2:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[CH:16](=[C:12]1[NH:11][C:10](=[O:24])[C:9](=[CH:8][C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:26][C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)=[CH:7][N:6]=2)[NH:14][C:13]1=[O:15])[C:17]1[CH:18]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of Compound C (1 g), 4-(bromomethyl)pyridine (2 g), sodium carbonate (2 g), and DMF (50 mL) were stirred at 100° C. for 16 hr and cooled at an ice bath to produce a yellow precipitate. The precipitate was then collected and washed with water to give 0.38 g (30%) of 3-benzylidene-6-((5-(pyridin-4-ylmethoxy)pyridin-2-yl)methylene)piperazine-2,5-dione (Compound 1). mp 254-255° C.; 1H-NMR (400 MHz, CDCl3), 5.26 (s, 2H) 6.78 (s, 1H), 7.11 (s, 1H), 7.31-7.59 (m, 9H), 8.20 (s, 1H), 8.48 (dd, J=2.8 Hz, 1H),), 8.72, (s, 2H), 12.50 (s, 1H).

Workup

temperaturecooled at an ice bath
customto produce a yellow precipitate
customThe precipitate was then collected
washwashed with water

Sources & evidence

ORD record: ord-083fcef9550c41fa804ce18d224d5664
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710062B2

Reaction notes

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