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

HRID 1692552Notes

Reaction equation

HRID 1692552 reaction equation
[CH2:1]([NH2:3])[CH3:2].[CH3:4][CH2:5][NH:6][C:7]([C@H:9]1[O:13][C@@H:12]([N:14]2[C:18]3[N:19]=[C:20]([C:24]#[C:25][CH2:26][CH:27]4[CH2:32][CH2:31][CH:30]([C:33](OC)=[O:34])[CH2:29][CH2:28]4)[N:21]=[C:22]([NH2:23])[C:17]=3[N:16]=[CH:15]2)[C@H:11]([OH:37])[C@@H:10]1[OH:38])=[O:8]>>[CH2:5]([NH:6][C:7]([CH:9]1[CH:10]([OH:38])[CH:11]([OH:37])[CH:12]([N:14]2[CH:15]=[N:16][C:17]3[C:18]2=[N:19][C:20]([C:24]#[C:25][CH2:26][CH:27]2[CH2:32][CH2:31][CH:30]([C:33](=[O:34])[NH:3][CH2:1][CH3:2])[CH2:29][CH2:28]2)=[N:21][C:22]=3[NH2:23])[O:13]1)=[O:8])[CH3:4]

Participants

3

Reactant 2

HCID 6341EthylamineHCID 9805430Apadenoson

Product 1

HCID 672812965-{6-Amino-2-[3-(4-ethylcarbamoyl-cyclohexyl)-prop-1-ynyl]-purin-9-yl}-3,4-dihydroxytetrahydrofuran-2-carboxylic acid ethylamideYield 73%

Conditions

Temperature
60 °C

Procedure

To a sealed tube containing 5 mL of freshly distilled ethylamine was added 10 mg (0.02 mmol) of ATL146e. The flask was sealed and allowed to stir at 60° C. for 80 hours. After this time the reaction was only about 50% complete by HPLC. The vessel was cooled to 0° C., opened, and the ethylamine was removed in vacuo to yield 4.5 mg (73%) of JR3037 as a white solid and the recovery of 4.0 mg of starting material after the residue was purified by RP-HPLC. 1H NMR (CD3OD-d4) δ. 13C NMR (CD3OD-d4) δ. APCI m/z (rel intensity) 500.8 (MH+, 100), 327.4 (3).

Workup

  1. customThe flask was sealed
  2. temperatureThe vessel was cooled to 0° C.
  3. customthe ethylamine was removed in vacuo

Sources & evidence

ORD record
ord-635e10ef0707430e8847358e2bf71caf
Source dataset
uspto-grants-2012_04
Patent number
US08158604B2

Reaction notes

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