Nanofin → HCID 58924881, compound

HRID 1991000Notes

Reaction equation

HRID 1991000 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([OH:9])=O)[N:6]=1.[CH3:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([CH3:17])[NH:12]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([N:12]2[CH:13]([CH3:17])[CH2:14][CH2:15][CH2:16][CH:11]2[CH3:10])=[O:9])[N:6]=1

Participants

7

Reactant 4

HCID 68843NanofinHCID 81531DiisopropylethylamineHCID 27632092-Bromo-1,3-thiazole-4-carboxylic acid2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 58924881HCID 58924881, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-bromothiazole-4-carboxylic acid (Intermediate 3; 2 g, 9.6 mmol), 2,6-dimethylpiperidine (1.18 mL, 8.8 mmol), HATU (4.18 g, 11.0 mmol) and DIEA (2.1 mL, 12.1 mmol) in DMF (10 mL) was stirred at room temperature for 1 h. Ethyl acetate (20 mL) was added and the solution was washed with 0.2 M HCl (2×10 mL), water (10 mL), and brine (10 mL), then it was dried (MgSO4), filtered, evaporated, and purified by flash column chromatography (10-40% ethyl acetate/hexanes) to give (2-bromo-thiazol-4-yl)-(2,6-dimethyl-piperidin-1-yl)-methanone (2.3 g, 86%) as a white solid.

Workup

  1. washthe solution was washed with 0.2 M HCl (2×10 mL), water (10 mL), and brine (10 mL)
  2. dry with materialit was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. custompurified by flash column chromatography (10-40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-0600275075234c788c26e3e962a29b2b
Source dataset
uspto-grants-2010_01
Patent number
US07645773B2

Reaction notes

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