2,4,6-Trimethylpyridine → HCID 70110228, 화합물

HRID 352248

반응식

HRID 352248 반응식
[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

참가 물질

10

반응물 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, 화합물

생성물 1

HCID 70110228HCID 70110228, 화합물수율 74%

시약·촉매·용매 4

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

실험 절차

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).

후처리

  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%

출처 및 근거

ORD 기록
ord-f916f7e25a7549a4a29505374dfffe9e
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743794B2

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