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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 513098
ノート
印刷プレビュー

反応式

HRID 513098 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

3

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

反応条件

温度
140 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-52a340757c034561a33233fc43a7350b
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09102676B2

反応ノート

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