Sodium Carbonate → 7-[(8-cyclopentyl-7,7-diethyl-5-methyl-6-oxo-pteridin-2-yl)amino]-N-(1-methyl-4-piperidyl)-2,3-dihydrobenzofuran-4-carboxamide

HRID 2364762노트

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HRID 2364762 반응식
[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([NH:16][C:17]4[CH:18]=[CH:19][C:20]([C:26]([OH:28])=O)=[C:21]5[C:25]=4[O:24][CH2:23][CH2:22]5)[N:12]=[CH:11][C:10]=3[N:9]([CH3:29])[C:8](=[O:30])[C:7]2([CH2:33][CH3:34])[CH2:31][CH3:32])[CH2:5][CH2:4][CH2:3][CH2:2]1.F[B-](F)(F)F.[N:40]1(OC(N(C)C)=[N+](C)C)[C:44]2[CH:45]=[CH:46]C=[CH:48][C:43]=2N=N1.[CH:57]([N:60](C(C)C)CC)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([NH:16][C:17]4[CH:18]=[CH:19][C:20]([C:26]([NH:40][CH:44]5[CH2:43][CH2:48][N:60]([CH3:57])[CH2:46][CH2:45]5)=[O:28])=[C:21]5[C:25]=4[O:24][CH2:23][CH2:22]5)[N:12]=[CH:11][C:10]=3[N:9]([CH3:29])[C:8](=[O:30])[C:7]2([CH2:31][CH3:32])[CH2:33][CH3:34])[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

6

반응물 4

HCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 681073747-[(8-Cyclopentyl-7,7-diethyl-5-methyl-6-oxo-pteridin-2-yl)amino]-2,3-dihydrobenzofuran-4-carboxylic acid

생성물 1

HCID 510367897-[(8-cyclopentyl-7,7-diethyl-5-methyl-6-oxo-pteridin-2-yl)amino]-N-(1-methyl-4-piperidyl)-2,3-dihydrobenzofuran-4-carboxamide수율 16.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

7-[(8-Cyclopentyl-7,7-diethyl-5-methyl-6-oxo-pteridin-2-yl)amino]-2,3-dihydrobenzofuran-4-carboxylic acid 42b (50 mg, 0.11 mmol) was dissolved in 20 mL of dichloromethane followed by the addition of O-(benzotriazol-1-yl)-N,N,N′,N′-tetra methyluronium tetrafluoroborate (35 mg, 0.11 mmol), diisopropylethylamine (31 mg, 0.24 mmol) and 1-methyl-piperidyl-4-yl-amine (13 mg, 0.11 mmol) successively. The reaction solution was stirred at room temperature for 1 hour. The resulting solution was added with 50 mL of saturated sodium carbonate solution and extracted with dichloromethane (100 mL×2). The combined organic phase was washed with water (20 mL) and saturated sodium chloride solution (20 mL) successively, then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography with elution system A to obtain the title compound 7-[(8-cyclopentyl-7,7-diethyl-5-methyl-6-oxo-pteridin-2-yl)amino]-N-(1-methyl-4-piperidyl)-2,3-dihydrobenzofuran-4-carboxamide 42 (10 mg, yield: 16.0%) as a white solid.

후처리

  1. extractionextracted with dichloromethane (100 mL×2)
  2. washThe combined organic phase was washed with water (20 mL) and saturated sodium chloride solution (20 mL) successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography with elution system

출처 및 근거

ORD 기록
ord-c6c1a5623d5644879bf453015349fe9b
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691822B2

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