Sodium Bicarbonate → HCID 86711375, compound

HRID 926300Notes

Reaction equation

HRID 926300 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:17]3[CH2:16][CH2:15][N:14]4[C:18](=[O:24])[CH2:19][NH:20][C:21](=[O:23])[CH2:22][CH:13]4[C:12]=3[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:17]3[CH2:16][CH2:15][N:14]4[C:18](=[O:24])[CH2:19][NH:20][C:21](=[O:23])[CH:22]=[C:13]4[C:12]=3[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 86711374HCID 86711374, compound

Product 1

HCID 86711375HCID 86711375, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
160 °C

Procedure

94-11. A mixture of 4-(6-fluoropyridin-3-yl)-5,6,9,10,12,12a-hexahydro-[1,4]diazepino[1,7-h][1,7]naphthyridine-8,11-dione (32 mg, 0.098 mmol) and SeO2 (19 mg, 0.17 mmol) in pyridine (1.5 mL) was stirred at 160° C. for 30 min under microwave conditions. The reaction mixture was allowed to warm to rt and poured into saturated aqueous NaHCO3 solution. The mixture was extracted with AcOEt (3×). The combined organic layers were dried with sodium sulfate, filtered and the solvent was removed under reduced pressure. The crude product was dried under high vacuo overnight to yield the title compound as a beige solid (32 mg) which was used without further purification in the next step. UPLC-MS: MS 325.2 (M+H+); UPLC rt 0.65 min.

Workup

  1. temperatureto warm to rt
  2. extractionThe mixture was extracted with AcOEt (3×)
  3. dry with materialThe combined organic layers were dried with sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. dry with materialThe crude product was dried under high vacuo overnight

Sources & evidence

ORD record
ord-16b18b57341b41259daa50fd6e527ce8
Source dataset
uspto-grants-2016_03
Patent number
US09284331B2

Reaction notes

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