Dimethylformamide → HCID 68184855, compound

HRID 2366978Notes

Reaction equation

HRID 2366978 reaction equation
[N:1]([CH2:4][CH2:5][OH:6])=[N+:2]=[N-:3].CN(C)C=O.CC([N:16]([C@H:20]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([C:30]#[CH:31])[CH:28]=2)[N:23]([C:32](=[O:34])[CH3:33])[C@@H:22]([CH3:35])[CH2:21]1)[C:17](=[O:19])[O-:18])(C)C>[Cu]I.CO>[C:32]([N:23]1[C:24]2[C:29](=[CH:28][C:27]([C:30]3[N:3]=[N:2][N:1]([CH2:4][CH2:5][OH:6])[CH:31]=3)=[CH:26][CH:25]=2)[C@H:20]([NH:16][C:17](=[O:19])[O:18][C:27]([CH3:30])([CH3:28])[CH3:26])[CH2:21][C@@H:22]1[CH3:35])(=[O:34])[CH3:33]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 1231182-AzidoethanolHCID 86669437HCID 86669437, compound

Product 1

HCID 68184855HCID 68184855, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolvent

Procedure

A flask was charged with 2-azidoethanol (318 mg, 3.65 mmol) and copper(I) iodide (17.40 mg, 0.091 mmol) then filled with N,N-dimethylformamide (DMF) (13 mL) and methanol (1.5 mL). This mixture was treated with 1,1-dimethylethyl[(2S,4R)-1-acetyl-6-ethynyl-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Intermediate 113) (600 mg, 1.827 mmol) and the resulting mixture was at 100° C. for 2 h under microwave irradiation then cooled to room temperature and partitioned between EtOAc and water. The layers were separated and the aqueous phase was extracted three times with EtOAc. The combined organic layers were washed twice with brine, and then dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 0 to 5% MeOH in DCM) gave 1,1-dimethylethyl {(2S,4R)-1-acetyl-6-[1-(2-hydroxyethyl)-1H-1,2,3-triazol-4-yl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate (659 mg, 1.523 mmol, 83% yield).

Workup

  1. customthe resulting mixture was at 100° C. for 2 h under microwave irradiation
  2. custompartitioned between EtOAc and water
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted three times with EtOAc
  5. washThe combined organic layers were washed twice with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by flash chromatography on silica gel (gradient: 0 to 5% MeOH in DCM)

Sources & evidence

ORD record
ord-e5f5f8b6a7d645b38b2bd2bb5e5b7b8f
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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