Acetic Acid → 1-{1-[4-(5-Methoxy-3-phenyl-1,6-naphthyridin-2-yl)benzyl]piperidin-4-yl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 604994노트

반응식

HRID 604994 반응식
[CH3:1][O:2][C:3]1[N:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:7]([C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1)=[N:8]2.[NH:27]1[CH2:32][CH2:31][CH:30]([N:33]2[C:37]3=[N:38][CH:39]=[N:40][C:41]([NH2:42])=[C:36]3[CH:35]=[N:34]2)[CH2:29][CH2:28]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C=O)C.CO>[CH3:1][O:2][C:3]1[N:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:7]([C:13]1[CH:14]=[CH:15][C:16]([CH2:17][N:27]3[CH2:32][CH2:31][CH:30]([N:33]4[C:37]5=[N:38][CH:39]=[N:40][C:41]([NH2:42])=[C:36]5[CH:35]=[N:34]4)[CH2:29][CH2:28]3)=[CH:19][CH:20]=1)=[N:8]2

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 577139461-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidin-4-amineHCID 598461374-(5-Methoxy-3-phenyl-1,6-naphthyridin-2-yl)benzaldehyde

생성물 1

HCID 598461511-{1-[4-(5-Methoxy-3-phenyl-1,6-naphthyridin-2-yl)benzyl]piperidin-4-yl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

A solution of 4-(5-methoxy-3-phenyl-1,6-naphthyridin-2-yl)benzaldehyde (80 mg, 0.235 mmol) and 1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine-4-amine (58 mg, 0.26 mmol) in dry DMF (1 mL) containing acetic acid (70 μL, 1.25 mmol) was stirred at room temperature 16 hours. Sodium triacetoxyborohydride (91 mg, 0.43 mmol) was then added to the semi-solid mixture and stirred for three hours. The mixture was diluted with methanol and the solvent evaporated. The residue was purified by column chromatography on silica gel eluting with a 0.5 to 5% methanol/ethyl acetate (sat'd NH3) gradient. The combined fractions were concentrated and the residue was digested with acetonitrile to afford upon cooling the pure title compound. 1H-NMR (500 MHz, CDCl3): δ 8.55 (1H, s), 8.39 (1H, s), 8.23 (1H, d, J=6 Hz), 7.92 (1H, s), 7.56 (1H, d, J=6 Hz), 7.41 (2H, d, J=7.8 Hz), 7.24-7.33 (5H, m), 5.40 (2H, br s), 4.75 (1H, m), 4.17 (3H, s), 3.57 (2H, br s), 2.31-2.41 (2H, m), 2.18-2.28 (2H, m), 1.96 (2H, br d, J=10.7 Hz). m/e (m+1): 543.3.

후처리

  1. stirringstirred for three hours
  2. customthe solvent evaporated
  3. customThe residue was purified by column chromatography on silica gel eluting with a 0.5 to 5% methanol/ethyl acetate (sat'd NH3) gradient
  4. concentrationThe combined fractions were concentrated
  5. customto afford

출처 및 근거

ORD 기록
ord-4d6ee85a731c4d99b00573089ad18324
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910561B2

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