5,6-Diamino-2-(2-(dimethylamino)ethyl)isoindoline-1,3-dione → 6-(2-(Dimethylamino)ethyl)-2-(2-methoxy-4-((1-phenylpropan-2-yl)oxy)pyridine-3-yl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione

HRID 69390노트

반응식

HRID 69390 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[C:7](=[O:12])[N:6]([CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[C:5]2=[O:18].[CH3:19][O:20][C:21]1[N:28]=[CH:27][CH:26]=[C:25]([O:29][CH:30]([CH3:38])[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:22]=1[CH:23]=O>CO.C(O)(=O)C>[CH3:17][N:15]([CH3:16])[CH2:14][CH2:13][N:6]1[C:5](=[O:18])[C:4]2[CH:3]=[C:2]3[NH:1][C:23]([C:22]4[C:21]([O:20][CH3:19])=[N:28][CH:27]=[CH:26][C:25]=4[O:29][CH:30]([CH3:38])[CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[N:11][C:10]3=[CH:9][C:8]=2[C:7]1=[O:12]

참가 물질

5

반응물 2

HCID 666864925,6-Diamino-2-(2-(dimethylamino)ethyl)isoindoline-1,3-dioneHCID 86663225HCID 86663225, 화합물

생성물 1

HCID 666906826-(2-(Dimethylamino)ethyl)-2-(2-methoxy-4-((1-phenylpropan-2-yl)oxy)pyridine-3-yl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione수율 69.2%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 887Methanol용매

실험 절차

5,6-Diamino-2-(2-(dimethylamino)ethyl)isoindoline-1,3-dione (0.47 g, 1.88 mmol) was dissolved in MeOH (30 mL) and acetic acid (10 mL). 2-Methoxy-4-((1-phenylpropan-2-yl)oxy)nicotinaldehyde (0.51 g, 1.88 mmol) was added under air at rt. The reaction mixture was stirred at rt under air overnight. The volatile was removed. The residue was subjected to column chromatography (silica-gel, CH2Cl2/MeOH=17/3 v/v) to give a white solid product, 0.65 g, 69.2% yield. MS: 500.3 [M+H]+. 1H-NMR (DMSO-d6, 500 MHz): δ 13.23 (s, 1H), 8.20 (d, 1H, J=6.0 Hz), 8.12 (s, 1H), 7.95 (s, 1H), 7.09-7.07 (m, 1H), 7.11-7.95 (m, 5H), 4.84-4.81 (m, 1H), 3.82 (s, 3H), 3.72 (t, 2H, J=6.5 Hz), 2.78 (d, 2H, J=6.0 Hz), 2.53 (t, 2H, J=6.5 Hz), 2.19 (s, 6H), 1.17 (d, 3H, J=6.0 Hz).

후처리

  1. customThe volatile was removed
  2. customto give a white solid product, 0.65 g, 69.2% yield

출처 및 근거

ORD 기록
ord-f8ec113d703b4848818788d634b28586
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822500B2

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