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Tert-butyl 2'-(2-(benzofuran-2-yl)pyrimidin-4-yl)-5'-(4-methoxybenzyl)-4'-oxo-1',4',5',6'-tetrahydrospiro[piperidine-4,7'-pyrrolo [3,2-c]pyridine]-1-carboxylate → 2'(2-(benzofuran-2-yl)pyrimidin-4-yl)-5',6'-dihydrospiro[piperidine-4,7'-pyrrolo[3,2-c]pyridin]-4'(1'H)-one

HRID 1618954
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HRID 1618954 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[N:15]=[C:14]([C:16]2[NH:24][C:23]3[C:22]4([CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]4)[CH2:21][N:20](CC4C=CC(OC)=CC=4)[C:19](=[O:46])[C:18]=3[CH:17]=2)[CH:13]=[CH:12][N:11]=1>C(O)(C(F)(F)F)=O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[N:15]=[C:14]([C:16]2[NH:24][C:23]3[C:22]4([CH2:25][CH2:26][NH:27][CH2:28][CH2:29]4)[CH2:21][NH:20][C:19](=[O:46])[C:18]=3[CH:17]=2)[CH:13]=[CH:12][N:11]=1
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참가 물질

3

반응물 1

HCID 68315015Tert-butyl 2'-(2-(benzofuran-2-yl)pyrimidin-4-yl)-5'-(4-methoxybenzyl)-4'-oxo-1',4',5',6'-tetrahydrospiro[piperidine-4,7'-pyrrolo [3,2-c]pyridine]-1-carboxylate

생성물 1

HCID 532465892'(2-(benzofuran-2-yl)pyrimidin-4-yl)-5',6'-dihydrospiro[piperidine-4,7'-pyrrolo[3,2-c]pyridin]-4'(1'H)-one수율 95.7%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

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온도
140 °C

실험 절차

A6 (3.60 g, 5.81 mmol) was dissolved in TFA (29.0 mL). The mixture was stirred at 140° C. for 40 min in the microwave. After cooling to room temperature, the reaction mixture was concentrated under vacuum. The crude product was purified by Strong Cation Exchange (SCX) with MeOH as eluent, followed by rinsing with 0.7 N NH3 in MeOH to obtain the pure free base as yellow solid (2.22 g). 1H NMR (400 MHz, DMSO-D6, 300K): δ=1.64 (2H, d, J=12.8 Hz), 2.15 (2H, br dt, J=13.0 Hz), 2.71 (2H, t, J=11.9 Hz), 2.89 (2H, d, J=11.2 Hz), 3.46 (2H, s), 4.12 (1H, br s), 7.24 (1H, s), 7.35 (1H, t, J=7.4 Hz), 7.37 (1H, s), 7.46 (1H, t, J=7.4 Hz), 7.75 (1H, d, J=8.2 Hz), 7.81 (1H, d, J=5.6 Hz), 7.83 (1H, d, J=8.6 Hz), 8.09 (1H, s), 8.76 (1H, d, J=5.4 Hz), 11.78 (1H, br s); MS (ES) C23H21N5O2 requires: 399. found: 400.1 [M+H]+.

후처리

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated under vacuum
  3. customThe crude product was purified by Strong Cation Exchange (SCX) with MeOH as eluent
  4. washby rinsing with 0.7 N NH3 in MeOH

출처 및 근거

ORD 기록
ord-50eba8f335e44d288fe69f6ce51ea3c5
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08772286B2

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