Sodium hydride → HCID 59783842, compound

HRID 1946582Notes

Reaction equation

Cl[C:2]1[N:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][CH:14]1[CH2:16][CH2:15]1)=[O:5].[H-].[Na+]>N1C=CC=CC=1>[CH:14]1([N:13]2[C:2]3[N:20]=[CH:19][CH:18]=[CH:17][C:3]=3[C:4](=[O:5])[NH:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]2=3)[CH2:16][CH2:15]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of title compound 80a (1.9 g, 6.6 mmol) in pyridine (60 mL) was added washed sodium hydride (0.8 g, 19.8 mmol, 60% in oil). Bubbling occurred and the clear solution turn yellow. The mixture was heated to 80° C. for 1 h and overnight at room temperature. It was then heated to 120° C. for 1 h (the mixture turned black). The mixture was cooled down to room temperature and 1N HCl (20 mL) was added slowly. This mixture was extracted with DCM (2×). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The crude was purified by flash chromatography (SiO2, 0% to 50% ethyl acetate in hexanes over 20 min then 50% for 10 min) to afford the title compound 81a (1.12 g, 68%) as a beige solid.

Workup

customBubbling
temperatureIt was then heated to 120° C. for 1 h (the mixture
temperatureThe mixture was cooled down to room temperature
addition1N HCl (20 mL) was added slowly
extractionThis mixture was extracted with DCM (2×)
dry with materialThe combined organic extracts were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe crude was purified by flash chromatography (SiO2, 0% to 50% ethyl acetate in hexanes over 20 min

Sources & evidence

ORD record: ord-4c58001deec64cf3899c2668e608ec50
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399452B2

Reaction notes

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