Dimethylformamide → HCID 23000187, compound

HRID 398373Notes

Reaction equation

HRID 398373 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:27])[N:11]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:12]([CH3:18])=[CH:13][C:14]=1[C:15](O)=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2[CH:39]=[CH:40][CH:41]=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)[CH:55]([CH3:57])[CH3:56].[CH3:61][N:62]([CH:64]=O)C>>[CH2:1]([O:8][C:9]1[C:10](=[O:27])[N:11]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:12]([CH3:18])=[CH:13][C:14]=1[C:15]([N:62]([CH2:64][CH:40]([CH3:39])[CH3:41])[CH2:61][CH:55]([CH3:57])[CH3:56])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 23000258HCID 23000258, compound

Product 1

HCID 23000187HCID 23000187, compound

Procedure

To a stirred solution of 3-benzyloxy-4-carboxy-6-methyl-1-tert-butyloxycarbonylmethyl-2-pyridinone from step 3 above (0.91 g, 2.3 mmol) in DMF (6 mL) was added dilsobutylamine (0.48 mL, 2.8 mmol), HATU (1.76 g, 4.6 mmol), and DIEA (0.45 mL, 2.6 mmol). The resulting solution was stirred at ambient temperature for 18 h. The solvents were removed in vacuo and the residue was purified by flash column chromatography using a gradient elution of 25-50% EtOAc:hexanes to give the title compound as an oil (0.80 g; HPLC RT 24.80 min, method B).

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was purified by flash column chromatography
  3. washa gradient elution of 25-50% EtOAc

Sources & evidence

ORD record
ord-0f42f5a908884eefaf27c6ca9362f030
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

Loading…