Trichloroisocyanuric Acid → 5-(4-Chloro-phenyl)-6-(2,4-dichloro-phenyl)-1-[4-(4-methyl-piperazin-1-ylmethyl)-phenyl]-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

HRID 1693537

반응식

HRID 1693537 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[CH:15]=[N:16][N:17]([C:18]4[CH:23]=[CH:22][C:21]([CH2:24]O)=[CH:20][CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2[Cl:33])=[CH:4][CH:3]=1.ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O.CC1(C)N([O])C(C)(C)CCC1.[CH3:57][N:58]1[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]1.C([BH3-])#N.[Na+]>C(Cl)Cl.CO.C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[CH:15]=[N:16][N:17]([C:18]4[CH:23]=[CH:22][C:21]([CH2:24][N:61]5[CH2:62][CH2:63][N:58]([CH3:57])[CH2:59][CH2:60]5)=[CH:20][CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2[Cl:33])=[CH:4][CH:3]=1

참가 물질

9

반응물 5

HCID 6909Trichloroisocyanuric AcidHCID 531671-MethylpiperazineHCID 2724126TempoHCID 5003444Sodium cyanoborohydrideHCID 578979015-(4-Chloro-phenyl)-6-(2,4-dichloro-phenyl)-1-(4-hydroxymethyl-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

생성물 1

HCID 578979205-(4-Chloro-phenyl)-6-(2,4-dichloro-phenyl)-1-[4-(4-methyl-piperazin-1-ylmethyl)-phenyl]-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

5-(4-Chloro-phenyl)-6-(2,4-dichloro-phenyl)-1-(4-hydroxymethyl-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (90.0 mg, 0.181 mmol) is dissolved in 10 mL of CH2Cl2. Trichloroisocyanuric acid (42.0 mg, 0.181 mmol) and TEMPO (1 mg) are added sequentially to the reaction mixture. The reaction mixture is allowed to stir for 30 min and the organic layer is washed with sodium bicarbonate and water, thus resulting in pure aldehyde. A portion of the aldehyde (40.0 mg, 0.0807 mmol) is dissolved in 2 mL of dry methanol. 200 μL of acetic acid and 100 μL of N-methylpiperazine are added to the reaction mixture and the mixture is allowed to stir for 10 min at room temp. Sodium cyanoborohydride (15 mg, 0.238 mmol) is added and the reaction mixture is stirred for 10 min and then quenched with ammonium hydroxide. The crude material is purified by column chromatography. 1H NMR (CDCl3, 400 MHz) δ 8.34(s, 1H), 8.06 (d, 2H), 7.44 (m, 2H), 7.34-7.28 (m, 3H), 7.18 (m, 2H), 7.03 (m, 1H), 5.31 (s, 2H), 3.66 (m, 2H), 2.89 (m, 6H), 2.71 (s, 3H). HPLC-MS calculated for C29H25Cl3N6O (M+H+) 579.1. Found: 579.1.

후처리

  1. washthe organic layer is washed with sodium bicarbonate and water
  2. customthus resulting in pure aldehyde
  3. stirringto stir for 10 min at room temp
  4. stirringthe reaction mixture is stirred for 10 min
  5. customquenched with ammonium hydroxide
  6. customThe crude material is purified by column chromatography

출처 및 근거

ORD 기록
ord-220614a997f74e9688db0575dc40944d
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158634B2

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