Apadenoson → 5-{6-Amino-2-[3-(4-carbamoyl-cyclohexyl)-prop-1-ynyl]-purin-9-yl}-3,4-dihydroxytetrahydrofuran-2-carboxylic acid ethylamide

HRID 16064

Reaktionsgleichung

Reaktionsgleichung von HRID 16064
[CH3:1][CH2:2][NH:3][C:4]([C@H:6]1[O:10][C@@H:9]([N:11]2[C:15]3[N:16]=[C:17]([C:21]#[C:22][CH2:23][CH:24]4[CH2:29][CH2:28][CH:27]([C:30]([O:32]C)=O)[CH2:26][CH2:25]4)[N:18]=[C:19]([NH2:20])[C:14]=3[N:13]=[CH:12]2)[C@H:8]([OH:34])[C@@H:7]1[OH:35])=[O:5].CO.[NH3:38]>>[CH2:2]([NH:3][C:4]([CH:6]1[CH:7]([OH:35])[CH:8]([OH:34])[CH:9]([N:11]2[CH:12]=[N:13][C:14]3[C:15]2=[N:16][C:17]([C:21]#[C:22][CH2:23][CH:24]2[CH2:25][CH2:26][CH:27]([C:30](=[O:32])[NH2:38])[CH2:28][CH2:29]2)=[N:18][C:19]=3[NH2:20])[O:10]1)=[O:5])[CH3:1]

Komponenten

3

Edukt 2

HCID 9805430ApadenosonHCID 21705897Ammonia methanol

Produkt 1

HCID 672812525-{6-Amino-2-[3-(4-carbamoyl-cyclohexyl)-prop-1-ynyl]-purin-9-yl}-3,4-dihydroxytetrahydrofuran-2-carboxylic acid ethylamideAusbeute 83 %

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a sealed tube containing 10 mL of saturated MeOH/NH3 solution was added 5 mg (0.01 mmol) of ATL146e. The flask was sealed and allowed to stir at 25° C. for 48 hours. The vessel was cooled to 0° C., opened, and the ammonia removed by bubbling N2 for 1 hour. The remaining solvent was then removed in vacuo to yield 4.0 mg (83%) of JR3055 as a white solid after the residue was purified by RP-HPLC. 1H NMR (CD3OD-d4) δ 8.41 (s, 1 H), 5.98 (d, J=7.2 Hz, 1H), 4.65 (dd, J=7.3 Hz, 4.8 Hz, 1 H), 4.41 (d, J=2.0 Hz, 1 H), 4.28 (dd, J=4.6 Hz, 2.0 Hz, 1 H), 3.35 (m, 2 H), 2.37 (d, J=6.4 Hz, 2 H) 2.10 (m, 1 H), 1.90 (m, _ H), 1.53 (m, _ H_), 1.23 (m, _ H), 1.12 (t, J=7.3 Hz, 3 H). 13C NMR (CD3OD-d4) δ. APCI m/z (rel intensity) 472.3 (MH+, 100), 299.4 (10).

Aufarbeitung

  1. customThe flask was sealed
  2. temperatureThe vessel was cooled to 0° C.
  3. customthe ammonia removed
  4. customby bubbling N2 for 1 hour
  5. customThe remaining solvent was then removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ccce973fdd0c4e37870ec91730cca6ba
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737127B2

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