2-Dimethylaminopyridine → HCID 18975311, compound

HRID 2393446Notes

Reaction equation

HRID 2393446 reaction equation
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([N:12]3[CH:16]=[N:15]C=N3)[CH:10]=2)[NH:5][CH:4]=1)=[O:2].[C:17]([O:21][C:22]([O:24]C(OC(C)(C)C)=O)=O)([CH3:20])([CH3:19])[CH3:18].[CH3:32][N:33](C1C=CC=CN=1)C>C(#N)C>[C:17]([O:21][C:22]([N:5]1[C:6]2=[CH:7][N:8]=[C:9]([N:12]3[CH:16]=[N:15][N:33]=[CH:32]3)[CH:10]=[C:11]2[C:3]([CH:1]=[O:2])=[CH:4]1)=[O:24])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 90495Di-tert-butyl dicarbonateHCID 86753094HCID 86753094, compound

Product 1

HCID 18975311HCID 18975311, compoundYield 435.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-formyl-5-(1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridine (1.1 g, 5.2 mmol) in acetonitrile (30 mL) was added di-tert-butyldicarbonate (1.69 g, 7.8 mmol) and dimethylaminopyridine (63 mg, 0.52 mmol) and the mixture was stirred at ambient temperature under nitrogen for 16 hours. The solvent was evaporated in vacuo and the residue chromatographed on silica eluting with a gradient of 2 to 5% MeOH in DCM to give a yellow solid. This was triturated with ether. The precipitate was collected by filtration to afford the title compound (0.71 g, 49%) as a cream solid. mp 170° C. (dec.). 1H NMR (360 MHz, d4 -MeOH) δ 1.76 (9H, s), 8.49 (1H, s), 8.80 (1H, s), 9.29 (2H, s), 9.34 (1H, s) and 10.12 (1H, s).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue chromatographed on silica eluting with a gradient of 2 to 5% MeOH in DCM
  3. customto give a yellow solid
  4. customThis was triturated with ether
  5. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-054bd34733a145c6b787f8fd76dd7909
Source dataset
uspto-grants-1998_09
Patent number
US05807857

Reaction notes

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