Sodium hydride → HCID 22036358, compound

HRID 493306Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:10][CH2:11][CH2:12][OH:13])[CH:3]=[CH:2]1.O1CCOCC1.[H-].[Na+].Cl[C:23]1[C:28]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[N:27][CH:26]=[CH:25][N:24]=1>O>[N:29]1([C:28]2[C:23]([O:13][CH2:12][CH2:11][O:10][C:8]3[CH:7]=[CH:6][CH:5]=[C:4]4[C:9]=3[NH:1][CH:2]=[CH:3]4)=[N:24][CH:25]=[CH:26][N:27]=2)[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1

Participants

Conditions

Temperature: 100 °C

Procedure

The product obtained in Step 1 above (0.200 g, 1 .13 mmol) and dioxane (4 mL) was placed in a reaction tube and NaH (60% in oil; 0.060 g, 1.50 mmol) was added. When the gas evolution had ceased, 2-chloro-3-(1-piperazinyl)pyrazine (0.228 g, 1.15 mmol. from Example 90, Step 1) was added and the tube sealed. The mixture was stirred at 100° C. for 3 h. After cooling, the reaction mixture was poured into water and extracted with EtOAc. The organic layer was extracted with 0.5 M aqueous HCl. The pH of the aqueous phase was adjusted to pH 11 with NaOH and extracted with EtOAc. The organic layer was dried (MgSO4) and concentrated to give 0.31 g (81%) of the title product. Pos-EI-MS shows M+ and 9 ions supporting the stated structure HRMS m/z calcd for C18H21N5O2 (M)+ 339.1695, found 339 1696.

Workup

customthe tube sealed
temperatureAfter cooling
extractionextracted with EtOAc
extractionThe organic layer was extracted with 0.5 M aqueous HCl
extractionextracted with EtOAc
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-4c3e993509b4410595d71983cd8829ca
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07534794B2

Reaction notes

Loading…