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

HRID 1823301노트

반응식

HRID 1823301 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7455c1c0ad314f899060cb06085884aa
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07037921B2

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