Diisopropylethylamine → 5'-Deoxy-5'-[[2-[[(1-ethoxyethylidene)amino]oxy]ethyl]methylamino]-8-(methylamino)adenosine

HRID 473570

반응식

HRID 473570 반응식
[CH2:1]([O:3][C:4](=[N:6][O:7][CH2:8][CH2:9][N:10]([CH3:30])[CH2:11][C@H:12]1[O:16][C@@H:15]([N:17]2[C:26]3[N:25]=[CH:24][N:23]=[C:21]([NH2:22])[C:20]=3[N:19]=[C:18]2C)[C@H:14]([OH:28])[C@@H:13]1[OH:29])[CH3:5])[CH3:2].[CH3:31][NH:32]C[C@H]1O[C@@H](N2C3N=CN=C(N)C=3N=C2NC)[C@H](O)[C@@H]1O.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:1]([O:3][C:4](=[N:6][O:7][CH2:8][CH2:9][N:10]([CH3:30])[CH2:11][C@H:12]1[O:16][C@@H:15]([N:17]2[C:26]3[N:25]=[CH:24][N:23]=[C:21]([NH2:22])[C:20]=3[N:19]=[C:18]2[NH:32][CH3:31])[C@H:14]([OH:28])[C@@H:13]1[OH:29])[CH3:5])[CH3:2]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 252327185'-Deoxy-5',8-bis(methylamino)adenosineHCID 866496695'-Deoxy-5'-[[2-[[(1-ethoxyethylidene)amino]oxy]ethyl]methylamino]-8-methyladenosine

생성물 1

HCID 866496685'-Deoxy-5'-[[2-[[(1-ethoxyethylidene)amino]oxy]ethyl]methylamino]-8-(methylamino)adenosine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Compound 6b was prepared by the same procedure as reported for 6a using 4c (500 mg, 1.61 mmol), ethyl N-(2-bromoethoxy)ethanamidate48 (407 mg, 1.93 mmol), DIEA (104 mg, 0.14 mL, 0.80 mmol), and DMF (5 mL). After column chromatography (elution with 7:1:0.3 chloroform:methanol:NH4OH), a yellow glassy sticky solid was obtained: yield 209 mg (30%), MS: m/z 439 (M+H)+; 1HNMR (DMSO-d6) δ 7.89 (s, 1H, H-2), 6.85 (q, 1H, 8CH3—NH), 6.47 (bs, 2H, 6-NH2), 5.69 (d, 1H, H-1′, J1′,2′=5.0 Hz), 5.27 (d, 1H, 2′-OH, J2′-2′OH=5.5 Hz), 5.06 (d, 1H, 3′-OH, J3′-3′OH=5.0 Hz), 4.88 (ddd, 1H, H-2′, J1′,2′=5.0 Hz, J2′,3′=5.8 Hz, J2′-2′OH=5.5 Hz), 4.17 (ddd, 1H, H-3′, J2′,3′=5.8 Hz, J3′,4′=4.7 Hz, J3′-3′OH=5.0 Hz), 3.86-3.95 (m, 3H, H-4′, NO—CH2), 3.92 (q, 2H, CH2CH3), 2.88 (d, 3H, 8NH—CH3, J=4.6 Hz), 2.71-2.77 (m, 1H, 5′-CH2), 2.56-2.67 (m, 3H, 5′-CH2, N(CH3)—CH2), 2.24 (s, 3H, N—CH3), 1.83 (s, 3H, C—CH3), 1.19 (t, 3H, OCH2CH3).

후처리

  1. washAfter column chromatography (elution with 7:1:0.3 chloroform:methanol:NH4OH)
  2. customa yellow glassy sticky solid was obtained

출처 및 근거

ORD 기록
ord-10e023d5058448bbb4471de317f772e4
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637485B2

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