2-Methoxypyrimidine-5-carboxaldehyde → 3-[5-(2-{(2-methoxyethyl)[(2-methoxy-5-pyrimidinyl)methyl]amino}ethoxy)-1H-indol-2-yl]-2(1H)-quinolinone

HRID 456901노트

반응식

HRID 456901 반응식
[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]1[C:19](=[O:28])[NH:20][C:21]3[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:12]2.[CH3:29][O:30][C:31]1[N:36]=[CH:35][C:34]([CH:37]=O)=[CH:33][N:32]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:37][C:34]1[CH:33]=[N:32][C:31]([O:30][CH3:29])=[N:36][CH:35]=1)[CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]1[C:19](=[O:28])[NH:20][C:21]3[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:12]2

참가 물질

5

반응물 3

HCID 31518662-Methoxypyrimidine-5-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 99077363-(5-{2-[(2-methoxyethyl)amino]ethoxy}-1H-indol-2-yl)-2(1H)-quinolinone

생성물 1

HCID 98272683-[5-(2-{(2-methoxyethyl)[(2-methoxy-5-pyrimidinyl)methyl]amino}ethoxy)-1H-indol-2-yl]-2(1H)-quinolinone

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

A solution of 3-(5-{2-[(2-methoxyethyl)amino]ethoxy}-1H-indol-2-yl)-2(1H)-quinolinone 2-1 (150 mg, 0.4 mmol), 2-methoxypyrimidine-5-carboxaldehyde (110 mg, 0.8 mmol) and sodium triacetoxyborohydride (168 mg, 0.8 mmol) in DCE (25 mL) was stirred under ambient conditions for 18 hours. The reaction mixture was concentrated, and the residue was partitioned between EtOAc and saturated NaHCO3 solution. The organic layer was washed with brine, dried over MgSO4 and concentrated. The residue was suspended in ethyl ether with the aid of sonication, then filtered and air dried to provide 3-[5-(2-{(2-methoxyethyl)[(2-methoxy-5-pyrimidinyl)methyl]amino} ethoxy)-1H-indol-2-yl]-2(1H)-quinolinone (2-2) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 11.05 (s, 1H), 9.60 (s, 1H), 8.53 (s, 2H), 8.33 (s, 1H), 7.68 (d, 1H, J=8 Hz), 7.52 (t, 1H, J=8 Hz), 7.34 (d, 1H, J=8 Hz), 7.27 (t, 1H, J=8 Hz), 7.22 (d, 1H, J=8 Hz), 7.05 (s, 1H), 6.96 (s, 1H), 6.86 (dd, 1H, J=8, 2 Hz), 4.13 (t, 2H, J=6 Hz), 4.01 (s, 3H), 3.80 (s, 2H), 3.53 (t, 2H, J=6 Hz), 3.34 (s, 3H), 3.01 (t, 2H, J=6 Hz), 2.84 (t, 2H, J=6 Hz).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between EtOAc and saturated NaHCO3 solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was suspended in ethyl ether with the aid of sonication
  7. filtrationfiltered
  8. customair dried

출처 및 근거

ORD 기록
ord-e005d4219d844909b227f40a3a3e0bcf
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186723B2

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