1-benzyl-1H-indole-3-carboxylic acid → 2-amino-7-(((1-benzyl-1H-indole-3-carbonyl)amino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester

HRID 1166804

반응식

HRID 1166804 반응식
C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC.[CH2:22]([N:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([C:38](O)=[O:39])=[CH:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:41]([O:45][C:46]([C:48]1[C:56]2[CH2:55][CH2:54][N:53]([CH2:57][C:58]3[CH:63]=[CH:62][C:61]([O:64][CH3:65])=[CH:60][CH:59]=3)[CH:52]([CH2:66][NH2:67])[C:51]=2[S:50][C:49]=1[NH2:68])=[O:47])([CH3:44])([CH3:43])[CH3:42]>O1CCCC1>[C:41]([O:45][C:46]([C:48]1[C:56]2[CH2:55][CH2:54][N:53]([CH2:57][C:58]3[CH:59]=[CH:60][C:61]([O:64][CH3:65])=[CH:62][CH:63]=3)[CH:52]([CH2:66][NH:67][C:38]([C:31]3[C:32]4[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=4)[N:29]([CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:30]=3)=[O:39])[C:51]=2[S:50][C:49]=1[NH2:68])=[O:47])([CH3:44])([CH3:42])[CH3:43]

참가 물질

6

반응물 4

HCID 336711-benzyl-1H-indole-3-carboxylic acidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 219366842-Amino-7-aminomethyl-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester

생성물 1

HCID 695597422-amino-7-(((1-benzyl-1H-indole-3-carbonyl)amino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester수율 51.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

Diisopropylethylamine (1.8 ml, 10.3 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (760 mg, 4.0 mmol) were added to a mixture of 1-benzyl-1H-indole-3-carboxylic acid (902 mg, 3.6 mmol) in tetrahydrofuran (50 ml). After stirring for 1 hour, the solution was cooled to 0° C. and a solution of 2-amino-7-aminomethyl-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester (700 mg, 1.7 mmol) in tetrahydrofuran (7 ml) was added dropwise. The reaction was allowed to slowly warm to room temperature. After 8 hours of stirring the solution was concentrated in vacuo and the residue dissolved in ethyl acetate (40 ml), washed with saturated aqueous sodium bicarbonate (2×30 ml), brine (1×30 ml), dried (MgSO4), filtered, and the solvent evaporated in vacuo. The residue was purified by silica gel chromatography using a mixture of hexane/ethyl acetate/triethylamine, (50:50:1) as eluent, which afforded 560 mg (51%) of 2-amino-7-(((1-benzyl-1H-indole-3-carbonyl)amino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester as a solid.

후처리

  1. temperatureto slowly warm to room temperature
  2. stirringAfter 8 hours of stirring the solution
  3. concentrationwas concentrated in vacuo
  4. dissolutionthe residue dissolved in ethyl acetate (40 ml)
  5. washwashed with saturated aqueous sodium bicarbonate (2×30 ml), brine (1×30 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent evaporated in vacuo
  9. customThe residue was purified by silica gel chromatography
  10. additiona mixture of hexane/ethyl acetate/triethylamine, (50:50:1) as eluent

출처 및 근거

ORD 기록
ord-93b393ceca034d42beafa6d8c608b5d6
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06613903B2

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