2-Aminothiazole → 4-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-N-(thiazol-2-yl)-benzamide

HRID 1988878Notes

Reaction equation

HRID 1988878 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[B:11]1[O:15][C:14]([CH3:17])([CH3:16])[C:13]([CH3:19])([CH3:18])[O:12]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:53][C:54]1[S:55][CH:56]=[CH:57][N:58]=1>CN(C=O)C>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:53][C:54]2[S:55][CH:56]=[CH:57][N:58]=2)=[O:7])=[CH:4][C:3]=1[B:11]1[O:12][C:13]([CH3:19])([CH3:18])[C:14]([CH3:17])([CH3:16])[O:15]1

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 160860864-Methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid2×

Product 1

HCID 219145174-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-N-(thiazol-2-yl)-benzamideYield 65.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid (Intermediate 4) (2.0 g) DIPEA (4-ml) and HATU (3.05 g) were dissolved in DMF (20 ml) and stirred at room temp for 15 min. 2-Aminothiazole (801 mg) was added and the mixture was stirred at room temp for 18 h. The solvent was evaporated under vacuum and the residue was partitioned between ethyl acetate (250 ml) and water (50 ml). The organic phase was washed with hydrochloric acid (2N, 50 ml) and aqueous sodium bicarbonate (1M, 50 ml) dried (magnesium sulphate) concentrated under vacuum. The residue was absorbed onto silica and purified by flash column chromatography eluting with cyclohexanelethyl acetate (4: 1) to give the title compound (1.72 g).

Workup

  1. stirringthe mixture was stirred at room temp for 18 h
  2. customThe solvent was evaporated under vacuum
  3. customthe residue was partitioned between ethyl acetate (250 ml) and water (50 ml)
  4. washThe organic phase was washed with hydrochloric acid (2N, 50 ml) and aqueous sodium bicarbonate (1M, 50 ml)
  5. dry with materialdried (magnesium sulphate)
  6. concentrationconcentrated under vacuum
  7. customThe residue was absorbed onto silica
  8. custompurified by flash column chromatography
  9. washeluting with cyclohexanelethyl acetate (4: 1)

Sources & evidence

ORD record
ord-17d3d5b43dc741a38d5fa2e15df9b9a6
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

Loading…