2,2-Dimethyl-1,3-dioxan-5-one → 3-(1-methylindol-3-yl)-4-[3-(2,2-dimethyl-1,3-dioxan-5-ylamino)phenyl]-1H-pyrrole-2,5-dione

HRID 1017577노트

반응식

HRID 1017577 반응식
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:24])[NH:13][C:14](=[O:23])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=2)=[CH:3]1.[CH3:25][C:26]1([CH3:33])[O:31][CH2:30][C:29](=O)[CH2:28][O:27]1.[BH3-]C#N.[Na+]>CO>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:24])[NH:13][C:14](=[O:23])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][CH:29]3[CH2:30][O:31][C:26]([CH3:33])([CH3:25])[O:27][CH2:28]3)[CH:17]=2)=[CH:3]1

참가 물질

5

반응물 3

HCID 27331412,2-Dimethyl-1,3-dioxan-5-oneHCID 5003444Sodium cyanoborohydrideHCID 5327711Iron oxide, spent

생성물 1

HCID 120181673-(1-methylindol-3-yl)-4-[3-(2,2-dimethyl-1,3-dioxan-5-ylamino)phenyl]-1H-pyrrole-2,5-dione수율 68.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of 3-(1-methylindol-3-yl)-4-(3-aminophenyl)-1H-pyrrole-2,5-dione (200 mg, 0.63 mmol) and 2,2-dimethyl-1,3-dioxane-5-one (98 mg, 0.76 mmol) in MeOH (10 mL) was stirred at room temperature for 15 min., and then NaCNBH3 (79 mg, 1.26 mmol) was added. After stirring the reaction mixture overnight the volatiles were removed under vacuo and the residue was purified by preparatory TLC (1% MeOH/CH2Cl2) to give 3-(1-methylindol-3-yl)-4-[3-(2,2-dimethyl-1,3-dioxan-5-ylamino)phenyl]-1H-pyrrole-2,5-dione (185 mg, 68%). MS(EI): M+ 431, MP: 201-203° C.

후처리

  1. stirringAfter stirring the reaction mixture overnight the volatiles
  2. customwere removed under vacuo
  3. customthe residue was purified by preparatory TLC (1% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-9b2e8560d3e44f178d286171522b73fa
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479490B2

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