Triethylamine → HCID 86684719, compound

HRID 339224Notes

Reaction equation

HRID 339224 reaction equation
I[C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C@@H:10]([O:15][CH2:16][C:17]2[C:18](=[O:32])[NH:19][C:20](=[O:31])[N:21]([CH:30]=2)[C@@H:22]2[O:29][C@H:26]([CH2:27][OH:28])[C@@H:24]([OH:25])[CH2:23]2)[C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([N+:33]([O-:35])=[O:34])[CH:3]=1.[CH2:36]([N-:39][C:40](=[O:45])[C:41]([F:44])([F:43])[F:42])[C:37]#[CH:38].CCN(CC)CC>CN(C=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I>[CH3:9][O:8][C:7]1[C:2]([C:38]#[C:37][CH2:36][NH:39][C:40](=[O:45])[C:41]([F:44])([F:43])[F:42])=[CH:3][C:4]([N+:33]([O-:35])=[O:34])=[C:5]([C@@H:10]([O:15][CH2:16][C:17]2[C:18](=[O:32])[NH:19][C:20](=[O:31])[N:21]([CH:30]=2)[C@@H:22]2[O:29][C@H:26]([CH2:27][OH:28])[C@@H:24]([OH:25])[CH2:23]2)[C:11]([CH3:14])([CH3:12])[CH3:13])[CH:6]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 86684720HCID 86684720, compoundHCID 178457782HCID 178457782, compound

Product 1

HCID 86684719HCID 86684719, compoundYield 91.8%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of compound 61 (80 mg, 0.13 mmol), N-propargyltrifluoroacetylamide (196 mg, 1.30 mmol), tetrakis(triphenylphosphine)-palladium(0) (30 mg, 0.026 mmol), CuI (9.9 mg, 0.052 mmol), and Et3N (80 μL) in anhydrous DMF (3.0 mL) was stirred at 50° C. for 12 hours. The mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography to yield 5-{(S)-1-[5-methoxy-4-(3-trifluoroacetamido-1-propynyl)-2-nitrophenyl]-2,2-dimethyl-propyloxy}methyl-2′-deoxyuridine 62 (75 mg, 90%). 1H NMR (400 MHz, MeOD-d4): δ 8.11 (s, 1H, H-6), 8.08 (s, 1H, Ph-H), 7.36 (s, 1H, Ph-H), 6.27 (t, 1H, J=6.4 Hz, H-1′), 5.33 (s, 1H, Ph-CH), 4.47 (m, 1H, H-3′), 4.44 (s, 2H, 5-CH2), 4.32 (d, 2H, J=2.0 Hz, CH2), 4.08 (s, 3H, OCH3), 3.99 (m, 1H, H-4′), 3.87 (m, 1H, H-5′a), 3.79 (m, 1H, H-5′b), 2.30 (m, 2H, H-2), 0.93 (s, 9H, C(CH3)3).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-910ce72135684fcfa05a9068a9d5370e
Source dataset
uspto-grants-2014_11
Patent number
US08889860B2

Reaction notes

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