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4-Iodo-2-methoxynicotinaldehyde → 4-[2-(4-Iodo-2-methoxy-pyridin-3-yl)-7-methyl-3H-benzoimidazol-5-yl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 1793724
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HRID 1793724 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([CH3:20])[C:17]([NH2:21])=[C:16]([NH2:22])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I:23][C:24]1[CH:29]=[CH:28][N:27]=[C:26]([O:30][CH3:31])[C:25]=1[CH:32]=O>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([CH3:20])[C:17]3[N:21]=[C:32]([C:25]4[C:26]([O:30][CH3:31])=[N:27][CH:28]=[CH:29][C:24]=4[I:23])[NH:22][C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

4

반응물 2

HCID 100383814-Iodo-2-methoxynicotinaldehydeHCID 235419144-(3,4-Diamino-5-methyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 235419074-[2-(4-Iodo-2-methoxy-pyridin-3-yl)-7-methyl-3H-benzoimidazol-5-yl]-piperazine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 887Methanol용매2회

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온도
0 °C

실험 절차

To a stirred solution of 4-(3,4-Diamino-5-methyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (44.6 mmol—assuming 100% conversion in previous step) in methanol (ca 2700 mL) at 0° C under a nitrogen atmosphere was slowly added (2 h) via addition funnel, a solution of 4-iodo-2-methoxy-pyridine-3-carbaldehyde (15.0 g, 57.1 mmol) in anhydrous methanol (225 mL). The resulting solution was then stirred at 0° C. for an additional 30 min, the cooling bath was removed, and the reaction mixture was allowed to stir at room temperature in the presence of air for 72 h. The resulting solution was concentrated in vacuo and the residue was dissolved in dichloromethane (1500 mL) and the solvent removed in vacuo (repeated 3×). The resulting dark foamy solid was dried under high vacuum. 1H NMR (500 MHz, CDCl3) δ 7.82 (d, 1H, J=5.4 Hz), 7.50 (d, 1H, J=5.4 Hz), 6.98 (brs, 1H), 6.90 (brs, 1H), 4.05 (s, 3H), 3.67–3.58 (m, 4H), 3.18–3.09 (m, 4H), 2.63 (s, 3H), 1.49 (s, 9H); LCMS (M+H)+ m/z 550.

후처리

  1. additionvia addition funnel
  2. customthe cooling bath was removed
  3. stirringto stir at room temperature in the presence of air for 72 h
  4. concentrationThe resulting solution was concentrated in vacuo
  5. dissolutionthe residue was dissolved in dichloromethane (1500 mL)
  6. customthe solvent removed in vacuo (repeated 3×)
  7. customThe resulting dark foamy solid was dried under high vacuum

출처 및 근거

ORD 기록
ord-94d85650d7304a0aa776d5e084ec41e8
출처 데이터셋
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07081454B2

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