Acetic Acid → 3-(3-methoxy-4-{[(5-methyl-2-furyl)methyl]amino}phenyl)-1-{1-[(1-methyl-1H-2-imidazolyl)methyl]-4-piperidyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 432520노트

반응식

HRID 432520 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:17]2[C:25]3[C:20](=[N:21][CH:22]=[N:23][C:24]=3[NH2:26])[N:19]([CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[N:18]=2)[CH:6]=[CH:7][C:8]=1[NH:9][CH2:10][C:11]1[O:12][C:13]([CH3:16])=[CH:14][CH:15]=1.[CH3:33][N:34]1[CH:38]=[CH:37][N:36]=[C:35]1[CH:39]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:17]2[C:25]3[C:20](=[N:21][CH:22]=[N:23][C:24]=3[NH2:26])[N:19]([CH:27]3[CH2:32][CH2:31][N:30]([CH2:39][C:35]4[N:34]([CH3:33])[CH:38]=[CH:37][N:36]=4)[CH2:29][CH2:28]3)[N:18]=2)[CH:6]=[CH:7][C:8]=1[NH:9][CH2:10][C:11]1[O:12][C:13]([CH3:16])=[CH:14][CH:15]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 223470923-(3-methoxy-4-{[(5-methyl-2-furyl)methyl]amino}phenyl)-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

생성물 1

HCID 223470863-(3-methoxy-4-{[(5-methyl-2-furyl)methyl]amino}phenyl)-1-{1-[(1-methyl-1H-2-imidazolyl)methyl]-4-piperidyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine수율 60%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

A mixture 3-(3-methoxy-4-{[(5-methyl-2-furyl)methyl]amino}phenyl)-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.045 g, 0.0001 mol), 1-methyl-2-imidazole carboxaldehyde (0.011 g, 0.00011 mol), and acetic acid (0.018 g, 0.0003 mol) in dichloroethane (4 mL) was stirred at room temperature under an atmosphere of nitrogen for 1.5 hrs. Sodium triacetoxyborohydride (0.064 g, 0.0003 mol) was added into the mixture and the mixture was stirred at ambient temperature under an atmosphere of nitrogen for 18 hours. The reaction was quenched with an aqueous 5 N solution of sodium hydroxide. The solvents were removed under reduced pressure, and the residue was partitioned between water and dichloromethane. The organic layer was washed with water and brine. The solvents were removed under reduced pressure. The residue was purified by RP-HPLC (Hypersilprep HS C18, 8 μm, 250×21.1 mm; 5%-100% over 35 min with 0.1 M ammonium acetate, 21 mL/min) to yield 3-(3-methoxy-4-{[(5-methyl-2-furyl)methyl]amino}phenyl)-1-{1-[(1-methyl-1H-2-imidazolyl)methyl]-4-piperidyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.03 g, 0.00006 mol).

후처리

  1. customThe reaction was quenched with an aqueous 5 N solution of sodium hydroxide
  2. customThe solvents were removed under reduced pressure
  3. customthe residue was partitioned between water and dichloromethane
  4. washThe organic layer was washed with water and brine
  5. customThe solvents were removed under reduced pressure
  6. customThe residue was purified by RP-HPLC (Hypersilprep HS C18, 8 μm, 250×21.1 mm; 5%-100% over 35 min with 0.1 M ammonium acetate, 21 mL/min)

출처 및 근거

ORD 기록
ord-c490fd2ef5c3480495b7a55becf4ae18
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660744B1

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