Nicotinic Acid → n-[3-(3-Methyl-oxo-5h-2-oxa-1,5,8-triaza-cyclopenta-[a]naphthalen-5-yl)-cyclohexylmethyl]-nicotinamide

HRID 1823306Notes

Reaction equation

HRID 1823306 reaction equation
I.[NH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH:6]([N:10]2[C:19]3[C:14](=[CH:15][N:16]=[CH:17][CH:18]=3)[C:13]3=[N:20][O:21][C:22]([CH3:23])=[C:12]3[C:11]2=[O:24])[CH2:5]1.[C:25](O)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[N:28][CH:27]=1.Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH3:23][C:22]1[O:21][N:20]=[C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[N:16][CH:15]=3)[N:10]([CH:6]3[CH2:7][CH2:8][CH2:9][CH:4]([CH2:3][NH:2][C:25](=[O:32])[C:26]4[CH:31]=[CH:30][CH:29]=[N:28][CH:27]=4)[CH2:5]3)[C:11](=[O:24])[C:12]=12

Participants

7

Reactant 5

HCID 938Nicotinic AcidHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 221701365-(3-aminomethyl-cyclohexyl)-3-methyl-5H-2-oxa-1,5,8-triaza-cyclopenta[a]naphthalen-4-one hydroiodide

Product 1

HCID 10273455n-[3-(3-Methyl-oxo-5h-2-oxa-1,5,8-triaza-cyclopenta-[a]naphthalen-5-yl)-cyclohexylmethyl]-nicotinamideYield 88.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine 5-(3-aminomethyl-cyclohexyl)-3-methyl-5H-2-oxa-1,5,8-triaza-cyclopenta[a]naphthalen-4-one hydroiodide (145 mg, 0.31 mmol) with nicotinic acid (45 mg, 0.36 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (70 mg, 0.36 mmol), 1-hydroxy-7-azabenzo-triazole (49 mg, 0.36 mmol), and N,N-diisopropylethyl amine (0.20 mL, 1.15 mmol), in N,N-dimethylformamide (4 mL) and stir over a weekend at ambient temperature. Concentrate in vacuo and take up in water and extract with dichloromethane. Dry over sodium sulfate and concentrate in vacuo. Eluted over silica gel using methanol/dichloromethane to give 115 mg (83%) of the desired amide as a solid. MS(ES): (M+1)+ 418.0,419.0 m/z.

Workup

  1. concentrationConcentrate in vacuo
  2. extractionextract with dichloromethane
  3. dry with materialDry over sodium sulfate
  4. concentrationconcentrate in vacuo
  5. washEluted over silica gel

Sources & evidence

ORD record
ord-5f1a62c38a474885953f75e2dca8f218
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

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