Sodium hydride → HCID 59783842, compound

HRID 1946620Notes

Reaction equation

HRID 1946620 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

4

Reactant 2

HCID 24758Sodium hydrideHCID 59783673HCID 59783673, compound

Product 1

HCID 59783842HCID 59783842, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Title compound 382 (0.7 g, 2.4 mmol), sodium hydride (0.292 g, 7.3 mmol) and pyridine (20 mL) were stirred together at 80° C. for 5 hours then at room temperature over week-end. The reaction mixture was then poured into an ice-water mixture and stirred for 1 hour. The beige solid was filtered and the filtrate was extracted with ethyl acetate (2 times). The combined organic extracts were dried and concentrated. The residue was purified by flash chromatography (10-70% ethyl acetate in hexanes). The 2 solids were mixed together to afford title compound 383 (0.51 g, 85%) as a beige solid. MS (m/z): 251.9 (M+H).

Workup

  1. waitat room temperature over week-end
  2. filtrationThe beige solid was filtered
  3. extractionthe filtrate was extracted with ethyl acetate (2 times)
  4. customThe combined organic extracts were dried
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (10-70% ethyl acetate in hexanes)
  7. additionThe 2 solids were mixed together

Sources & evidence

ORD record
ord-60480cb3ca9a4ae488cf06f5216206c4
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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