Triethylamine → HCID 86630120, compound

HRID 1014964Notes

Reaction equation

HRID 1014964 reaction equation
I[C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].C(N(CC)CC)C.[CH2:28]([CH:31]1[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[Cl:46])=[O:38])[CH2:33][CH2:32]1)[C:29]#[CH:30]>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.[Cu]I.CN(C=O)C>[Cl:46][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=1[O:39][C:37]([N:34]1[CH2:33][CH2:32][CH:31]([CH2:28][C:29]#[C:30][C@@:9]2([N:8]3[C:18]4[N:19]=[CH:2][N:3]=[C:4]([NH2:20])[C:5]=4[N:6]=[CH:7]3)[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]2[OH:11])[CH2:36][CH2:35]1)=[O:38]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 1696622-IodoadenosineHCID 578388912-Chlorophenyl 4-(prop-2-ynyl)piperidine-1-carboxylate

Product 1

HCID 86630120HCID 86630120, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-iodoadenosine (0.602 g, 1.531 mmol) in freshly degassed DMF (20 mL) was added degassed triethylamine (1.20 mL, 8.54 mmol), Pd(PPh3)4 (85 mg, 0.074 mmol), CuI (catalytic), and 2-chlorophenyl 4-(prop-2-ynyl)piperidine-1-carboxylate (0.588 g, 2.117 mmol). The mixture was stirred at room temperature under and inert atmosphere for 20 h. Silica bound Pd(II) scavenger Si-thiol (400 mg) and Pd(0) scavenger Si-TAAcOH (619 mg) were added and stirring continued a further 72 h. The suspension was filtered through celite and the resulting solution evaporated to dryness. The crude was purified by column chromatography, eluting with a gradient of DCM/MeOH (0-4%) to afford the pure product as a white solid: yield 0.733 g, 88%.

Workup

  1. additionwere added
  2. stirringstirring
  3. waitcontinued a further 72 h
  4. filtrationThe suspension was filtered through celite
  5. customthe resulting solution evaporated to dryness
  6. customThe crude was purified by column chromatography
  7. washeluting with a gradient of DCM/MeOH (0-4%)

Sources & evidence

ORD record
ord-e664c5c0f7ed418ba86e4a826791eb5f
Source dataset
uspto-grants-2011_07
Patent number
US07985754B2

Reaction notes

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