Benzoic Acid → HCID 67425493, compound

HRID 2383467Notes

Reaction equation

HRID 2383467 reaction equation
FC(F)(F)C(O)=O.[CH:8]1[C:20]2[C:19]3[CH2:18][CH2:17][NH:16][CH2:15][C:14]=3[CH:13]=[N:12][C:11]=2[NH:10][N:9]=1.[C:21](O)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[OH-].[Na+]>CCOC(C)=O.CCN(CC)CC.CN(C)C=O.CC(N(C)C)=O>[CH:8]1[C:20]2[C:19]3[CH2:18][CH2:17][N:16]([C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[O:28])[CH2:15][C:14]=3[CH:13]=[N:12][C:11]=2[NH:10][N:9]=1

Participants

9

Reactant 4

HCID 243Benzoic AcidHCID 14798Sodium HydroxideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67436402HCID 67436402, compound

Product 1

HCID 67425493HCID 67425493, compoundYield 15%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To 6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine trifluoroaceate salt was added benzoic acid (0.064 g, 0.52 mmol), dimethyl acetamide (4 mL), dimethylformamide (2 mL) and Et3N (1.0 mL). The mixture was vortexed to ensure that the solid was fully in solution before adding HBTU (0.20 g, 0.52 mmol). The reaction mixture was shaken at room temperature for 16 hours. On completion of the reaction, EtOAc (20 mL) and 1.5M NaOH (10 mL) was added to the reaction mixture. The organic layer was separated, washed with water (2×20 mL) and concentrated under reduce pressure. The crude product was purified using flash column chromatography (SiO2, 80% EtOAc in hexanes) to give the desired product, (8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)(phenyl)methanone (0.20 g, 15%) as a white solid. M.p.=198-200° C.; 1H NMR (400 MHz, DMSO-d6) δ13.60 (s, 1H), 8.44 & 8.15 (m, 2H), 7.49 (m, 5H), 4.90 & 4.71 (m, 2H), 4.02 & 3.66 (m, 2H), 3.16 (m, 2H); LCMS [M+H]: 279.

Workup

  1. additionwas added to the reaction mixture
  2. customThe organic layer was separated
  3. washwashed with water (2×20 mL)
  4. concentrationconcentrated
  5. customThe crude product was purified

Sources & evidence

ORD record
ord-2369562c35af4238a1338e35b4be15e8
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

Loading…