Ammonium formate → HCID 69809571, compound

HRID 1029076Notes

Reaction equation

C(N[C:9]1[CH:10]=[C:11]2[C:16](=[N:17][CH:18]=1)[NH:15][C:14](=[O:19])[C:13]1[CH:20]=[CH:21][CH:22]=[CH:23][C:12]2=1)C1C=CC=CC=1.C([O-])=O.[NH4+:27]>CO.[Pd]>[CH2:11]([NH:27][C:21]1[CH:22]=[CH:23][C:12]2[C:11]3[C:16](=[N:17][CH:18]=[CH:9][CH:10]=3)[NH:15][C:14](=[O:19])[C:13]=2[CH:20]=1)[C:12]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

2-Benzylamino-5H-benzo[c][1,8]naphthyridin-6-one (100 mg, 0.33 mmol), ammonium formate (209 mg, 3.30 mmol), and palladium/carbon (200 mg, 10% weight) were suspended in MeOH (6 mL) and stirred overnight at 60° C. The reaction mixture was filtered through celite, and the celite was washed with methanol. The filtrate was concentrated, and the crude product was purified via prep-LC-MS to provide 19 (10 mg, 14% yield) as a yellow solid. LC-MS (M+H=212, obsd.=212). 1H NMR (400 MHz, d6-DMSO): δ 11.63 (s, 1H), 8.31 (d, 1H), 8.28 (d, 1H), 7.96 (d, 1H), 7.85 (m, 2H), 7.64 (t, 1H), 7.31 (m, 1H), 7.24 (m, 1H).

Workup

filtrationThe reaction mixture was filtered through celite
washthe celite was washed with methanol
concentrationThe filtrate was concentrated
customthe crude product was purified via prep-LC-MS

Sources & evidence

ORD record: ord-cb021b3fef574e74bc4e06acbf4b73c9
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735584B2

Reaction notes

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