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

HRID 16065Notes

Reaction equation

HRID 16065 reaction equation
[CH3:1][NH2:2].[CH3:3][CH2:4][NH:5][C:6]([C@H:8]1[O:12][C@@H:11]([N:13]2[C:17]3[N:18]=[C:19]([C:23]#[C:24][CH2:25][CH:26]4[CH2:31][CH2:30][CH:29]([C:32]([O:34]C)=O)[CH2:28][CH2:27]4)[N:20]=[C:21]([NH2:22])[C:16]=3[N:15]=[CH:14]2)[C@H:10]([OH:36])[C@@H:9]1[OH:37])=[O:7]>CO>[CH2:4]([NH:5][C:6]([CH:8]1[CH:9]([OH:37])[CH:10]([OH:36])[CH:11]([N:13]2[CH:14]=[N:15][C:16]3[C:17]2=[N:18][C:19]([C:23]#[C:24][CH2:25][CH:26]2[CH2:31][CH2:30][CH:29]([C:32](=[O:34])[NH:2][CH3:1])[CH2:28][CH2:27]2)=[N:20][C:21]=3[NH2:22])[O:12]1)=[O:7])[CH3:3]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 9805430Apadenoson

Product 1

HCID 672805625-{6-Amino-2-[3-(4-methylcarbamoyl-cyclohexyl)-prop-1-ynyl]purin-9-yl}-3,4-dihydroxytetrahydrofuran-2-carboxylic acid ethylamideYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a sealed tube containing 10 mL 2.0 M methylamine in methanol was added 16.5 mg (0.03 mmol) of ATL146e. The flask was sealed and allowed to stir at 70° C. for 120 hours. The vessel was cooled to 0° C., opened, and the solvent was removed in vacuo to yield 8.0 mg (48%) of JR3065 as a white solid after the residue was purified by RP-HPLC. 1H NMR (CD3OD-d4) δ. 13C NMR (CD3OD-d4) δ. APCI m/z (rel intensity) 486.3 (MH+, 100), 313.4 (35).

Workup

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

Sources & evidence

ORD record
ord-725c15caf0dc4b3d8c11ea508702542d
Source dataset
uspto-grants-2010_06
Patent number
US07737127B2

Reaction notes

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