Nicotinic Acid → n-[3-(3-Methyl-4-oxo-5h-2-oxa-1,5,6-triaza-cyclopenta-[a]naphthalen-5-yl)-cyclohexylmethyl]-nicotinamide

HRID 1823301Notes

Reaction equation

HRID 1823301 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][CH:16]=[CH:17][N: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](=[N:18][CH:17]=[CH: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 221701525-(3-Aminomethyl-cyclohexyl)-3-methyl-5h-2-oxa-1,5,6-triaza-cyclopenta[a]naphthalen-4-one hydroiodide

Product 1

HCID 9888205n-[3-(3-Methyl-4-oxo-5h-2-oxa-1,5,6-triaza-cyclopenta-[a]naphthalen-5-yl)-cyclohexylmethyl]-nicotinamideYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine 5-(3-aminomethyl-cyclohexyl)-3-methyl-5H-2-oxa-1,5,6-triaza-cyclopenta[a]naphthalen-4-one hydroiodide (200 mg, 0.45 mmol) with nicotinic acid (56 mg, 0.45 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (87 mg, 0.45 mmol), 1-hydroxy-7-azabenzo-triazole (62 mg, 0.45 mmol), and N,N-diisopropylethyl amine (0.24 mL, 1.38 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 ethyl acetate. Dry over sodium sulfate and concentrate in vacuo. Elute over silica gel using methanol/dichloromethaneto give 88 mg (47%) of the desired amide as a light tan solid. MS(ES): (M+1)+ 418.2, 419.2 m/z.

Workup

  1. concentrationConcentrate in vacuo
  2. extractionextract with ethyl acetate
  3. dry with materialDry over sodium sulfate
  4. concentrationconcentrate in vacuo
  5. washElute over silica gel

Sources & evidence

ORD record
ord-7455c1c0ad314f899060cb06085884aa
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

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