Methyl 4-prop-2-ynylcyclohexanecarboxylate → Apadenoson

HRID 430396Notes

Reaction equation

HRID 430396 reaction equation
[NH2:1][C:2]1[N:10]=[C:9](I)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:12]1[O:16][C@H:15]([C:17]([NH:19][CH2:20][CH3:21])=[O:18])[C@@H:14]([OH:22])[C@H:13]1[OH:23].[CH2:24]([CH:27]1[CH2:32][CH2:31][CH:30]([C:33]([O:35][CH3:36])=[O:34])[CH2:29][CH2:28]1)[C:25]#[CH:26]>C(#N)C.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:21][CH2:20][NH:19][C:17]([C@H:15]1[O:16][C@@H:12]([N:6]2[C:7]3[N:8]=[C:9]([C:26]#[C:25][CH2:24][CH:27]4[CH2:32][CH2:31][CH:30]([C:33]([O:35][CH3:36])=[O:34])[CH2:29][CH2:28]4)[N:10]=[C:2]([NH2:1])[C:3]=3[N:4]=[CH:5]2)[C@H:13]([OH:23])[C@@H:14]1[OH:22])=[O:18]

Participants

6

Reactant 2

HCID 10749876Methyl 4-prop-2-ynylcyclohexanecarboxylateHCID 11697766(2s,3s,4r,5r)-5-(6-Amino-2-Iodo-9h-Purin-9-Yl)-N-Ethyl-3,4-Dihydroxytetrahydrofuran-2-Carboxamide

Product 1

HCID 9805430ApadenosonYield 24%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a degassed solution of 25 mg (0.063 mmol) of [(2S,3S,4R,5R)-5-(6-amino-2-iodopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]-N-ethylcarboxamide (6.9), 16.9 mg (0.094 mmol) (5.5), and 0.75 mg CuI in 5 mL each of TEA and acetonitrile was added 15 mg of Pd(PPh3)4. The solution was stirred for 24 hours at 70° C. after which time the solution was filtered through celite and chromatographed on silica gel with MeOH-CHCl3 (5:95) to give DWH-146e (24%).

Workup

  1. filtrationwas filtered through celite
  2. customchromatographed on silica gel with MeOH-CHCl3 (5:95)

Sources & evidence

ORD record
ord-cab41cf2de6b4f069c7845e0dd99bee8
Source dataset
uspto-grants-2001_11
Patent number
US06322771B1

Reaction notes

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