2,4,6-Trimethylpyridine → HCID 70110228、化合物

HRID 352248

反応式

HRID 352248 の反応式
[NH2:1][CH:2]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:3]([NH:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH:8]([N:12]2[C:21]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:22])[C:16]=3[C:15]3=[N:23][O:24][C:25]([CH3:26])=[C:14]3[C:13]2=[O:27])[CH2:7]1)=[O:4].Cl.[CH3:35][N:36]1[CH2:41][CH2:40][CH:39]([C:42](O)=[O:43])[CH2:38][CH2:37]1.Cl.CN(C)CCCN=C=NCC.CC1C=C(C)C=C(C)N=1.ON1C2N=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C.O.C([O-])(O)=O.[Na+]>[Cl:22][C:17]1[C:16]2[C:15]3[C:14](=[C:25]([CH3:26])[O:24][N:23]=3)[C:13](=[O:27])[N:12]([CH:8]3[CH2:9][CH2:10][CH2:11][CH:6]([NH:5][C:3]([CH:2]([NH:1][C:42]([CH:39]4[CH2:40][CH2:41][N:36]([CH3:35])[CH2:37][CH2:38]4)=[O:43])[C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)=[O:4])[CH2:7]3)[C:21]=2[CH:20]=[CH:19][CH:18]=1

参加物

10

反応物 5

HCID 79532,4,6-TrimethylpyridineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27600434-Piperidinecarboxylic acid, 1-methyl-, hydrochloride (1:1)HCID 22713739HCID 22713739、化合物

生成物 1

HCID 70110228HCID 70110228、化合物収率 74%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

A product from Example 638 (50 mg; 0.108 mmol) was dissolved in anhydrous dimethylformamide (10 mL) under a nitrogen atmosphere, mixed with 1-methyl-piperidine-4-carboxylic acid hydrochloride (58.0 mg; 0.323 mmol; 3 equiv), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (61.8 mg; 0.323 mmol; 3 equiv), 2,4,6-trimethylpyridine (86 μL; 0.645 mmol; 6 equiv), and 1-hydroxy-7-azabenzotriazole (43.9 mg; 0.323 mmol; 3 equiv), and stirred overnight at room temperature. The reaction solution was diluted with 2 volumes ethyl acetate, 10 volumes water, and 1 volume saturated NaHCO3(aq). The organic layer was separated and then washed with saturated NaCl(aq), dried over Na2SO4(S), filtered, and concentrated in vacuo. The resulting material was purified by radial chromatography on a 2 mm thick silica gel rotor with a 2% then 4% methanol/dichloromethane (v/v) mobile phase and finally a 2% methanol/0.5% triethylamine/dichloromethane (v/v/v) mobile phase. The desired product was isolated as a white solid in 74% yield (47 mg).

後処理

  1. customThe organic layer was separated
  2. washwashed with saturated NaCl(aq)
  3. dry with materialdried over Na2SO4(S)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting material was purified by radial chromatography on a 2 mm thick silica gel rotor with a 2%

出典と根拠

ORDレコード
ord-f916f7e25a7549a4a29505374dfffe9e
出典データセット
uspto-grants-2004_06
特許番号
US06743794B2

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