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

HRID 1823302ノート

反応式

HRID 1823302 の反応式
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]=[CH: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]=[CH:28][CH:27]=4)[CH2:5]3)[C:11](=[O:24])[C:12]=12

参加物

7

反応物 5

HCID 243Benzoic 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

生成物 1

HCID 10180152n-[3-(3-Methyl-4-oxo-5h-2-oxa-1,5,6-triaza-cyclopenta[a]naphthalen-5-yl)-cyclohexylmethyl]-benzamide収率 75.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Combine 5-(3-aminomethyl-cyclohexyl)-3-methyl-5H-2-oxa-1,5,6-triaza-cyclopenta[a]naphthalen-4-one hydroiodide (100 mg, 0.23 mmol) with benzoic acid (28 mg, 0.23 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (44 mg, 0.23 mmol), 1-hydroxy-7-azabenzo-triazole (31 mg, 0.23 mmol), and N,N-diisopropylethyl amine (0.12 mL, 0.69 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. Eluted over silica gel using methanol/dichloromethane to give 72 mg (75%) of the desired amide as an off white solid. MS(ES): (M+1)+ 417.2, 418.2 m/z.

後処理

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

出典と根拠

ORDレコード
ord-0f1f16fe39474505ac8f0feeae826dce
出典データセット
uspto-grants-2006_05
特許番号
US07037921B2

反応ノート

読み込み中…