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Triethylamine → 4-[4-amino-4-(4-chlorobenzyl)-piperidin-1-yl]-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester

HRID 2401570
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인쇄 미리보기

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HRID 2401570 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[C:8]2[CH:14]=C[NH:12][C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2].Cl.[Cl:17][C:18]1[CH:31]=[CH:30][C:21]([CH2:22][C:23]2([NH2:29])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:20][CH:19]=1.C([N:34](CC)CC)C>C(O)CCC.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([N:26]2[CH2:25][CH2:24][C:23]([NH2:29])([CH2:22][C:21]3[CH:20]=[CH:19][C:18]([Cl:17])=[CH:31][CH:30]=3)[CH2:28][CH2:27]2)=[C:8]2[CH:14]=[N:34][NH:12][C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2]
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참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 53438275Ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylateHCID 668730314-(4-Chlorobenzyl)-piperidin-4-ylamine hydrochloride

생성물 1

HCID 578991924-[4-amino-4-(4-chlorobenzyl)-piperidin-1-yl]-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester수율 87%

시약·촉매·용매 2

HCID 2631-Butanol
용매
HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid ethyl ester (Example 68A) (50 mg, 0.22 mmol), 4-(4-chlorobenzyl)-piperidin-4-ylamine hydrochloride (65 mg, 0.22 mmol) and triethylamine (150μ) in n-butanol (1.5 mL) was irradiated in a microwave reactor (200W) for 1 hr at 100° C. After cooling, the solvent was evaporated. The solids obtained were dissolved in ethyl acetate, the organic layer was washed with aqueous sodium hydrogen carbonate, brine and then dried (Na2SO4). Evaporation of the organic solution gave 4-[4-amino-4-(4-chlorobenzyl)-piperidin-1-yl]-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester as an off-white solid (80 mg, 87%). LC-MS (LCT2) m/z 415 [M+H+], Rt 3.99 min.

후처리

  1. temperatureAfter cooling
  2. customthe solvent was evaporated
  3. customThe solids obtained
  4. washthe organic layer was washed with aqueous sodium hydrogen carbonate, brine
  5. dry with materialdried (Na2SO4)
  6. customEvaporation of the organic solution

출처 및 근거

ORD 기록
ord-096230e6b5f445b199be22a3552e560d
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08796293B2

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