Propargyl alcohol → HCID 86654732, compound

HRID 2092848Notes

Reaction equation

HRID 2092848 reaction equation
I[C:2]1[C:3]2[CH2:33][NH:32][C:31](=[O:34])[C:4]=2[C:5]([NH:23][C:24]2[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=2)=[N:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19].[CH2:35]1C[O:38][CH2:37][CH2:36]1.CCN(CC)CC.C(O)C#C>CCOC(C)=O.[Cu]I.[Pd](Cl)Cl.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>[OH:38][CH2:37][C:36]#[C:35][C:2]1[C:3]2[CH2:33][NH:32][C:31](=[O:34])[C:4]=2[C:5]([NH:23][C:24]2[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=2)=[N:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21]

Participants

8

Reactant 4

HCID 7859Propargyl alcoholHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 86654729HCID 86654729, compound

Product 1

HCID 86654732HCID 86654732, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To an oven dried glass pressure vessel was added tert-butyl (1S,2R)-2-(7-iodo-3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate (25 mg, 0.043 mmol), copper(I) iodide (12.37 mg, 0.065 mmol), bis(triphenylphosphine) palladium(II) chloride (9.12 mg, 0.013 mmol), butylated hydroxytoluene (one granule), THF (866 μL), and Et3N (121 μL, 0.866 mmol). The mixture was degassed 3 min with nitrogen. Propargyl alcohol (31 μL, 0.520 mmol) was added and the vessel was capped and heated at 80° C. with stirring for 2 h and then at RT for 12 h. The reaction mixture was diluted with EtOAc (10 mL) and washed with water (5 mL) and brine (5 mL). The organic layer was collected, dried with Na2SO4, and concentrated to give the title compound as a brown residue, which was used without further purification (22 mg, 101%). [M+H] calc'd for C28H35N5O4, 506. found, 506.

Workup

  1. customTo an oven dried glass pressure vessel
  2. customThe mixture was degassed 3 min with nitrogen
  3. customthe vessel was capped
  4. waitat RT for 12 h
  5. washwashed with water (5 mL) and brine (5 mL)
  6. customThe organic layer was collected
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d21478c74ca947b4b742e452b08fae7e
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Reaction notes

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