Ammonium Hydroxide → 6-Isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridine-9-carboxamide

HRID 2193018Notes

Reaction equation

HRID 2193018 reaction equation
[CH:1]([C:4]1[C:13]2[CH:14]=[CH:15][C:16]([C:18](O)=[O:19])=[CH:17][C:12]=2[C:11]2[C:10](=[O:21])[NH:9][CH:8]=[CH:7][C:6]=2[N:5]=1)([CH3:3])[CH3:2].C(N1C=CN=C1)([N:24]1C=CN=C1)=O.[OH-].[NH4+]>CN(C=O)C>[CH:1]([C:4]1[C:13]2[CH:14]=[CH:15][C:16]([C:18]([NH2:24])=[O:19])=[CH:17][C:12]=2[C:11]2[C:10](=[O:21])[NH:9][CH:8]=[CH:7][C:6]=2[N:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 674172396-Isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridine-9-carboxylic acid

Product 1

HCID 593754536-Isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridine-9-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of 6-isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridine-9-carboxylic acid (78 mg, 0.28 mmol) in DMF (1.0 mL) was added 1,1′-carbonylbis(1H-imidazole) (CDI, 68 mg, 0.42 mmol). The reaction mixture was stirred for 1 hour at room temperature. Ammonium hydroxide (0.19 mL, 1.3 mmol) was added, and the resulting mixture was stirred for 15 minutes. The reaction mixture was diluted with DMF and purified directly by preparative reverse phase HPLC, eluting with an acetonitrile/water (with 0.05% TFA modifier) gradient to afford 6-isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridine-9-carboxamide. 1H NMR (500 MHz, DMSO-D6) δ 11.86 (s, 1H), 10.46 (s, 1H), 8.50 (d, 1H), 8.20 (s, 1H), 8.09 (d, 1H), 7.61 (s, 1H), 7.56 (t, 1H), 6.78 (d, 1H), 4.12 (septet, 1H), 1.37 (d, 6H). LRMS (ESI) calc'd for (C16H15N3O2) [M+H]+, 282.1; found 282.1.

Workup

  1. stirringthe resulting mixture was stirred for 15 minutes
  2. custompurified directly by preparative reverse phase HPLC
  3. washeluting with an acetonitrile/water (with 0.05% TFA modifier) gradient

Sources & evidence

ORD record
ord-81d5fd2c100a470db7f96d97fd301e29
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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