Acetic Anhydride → N-[[2-[(2R,6S)-2,6-dimethyl-4-morpholinyl]-5-(2,6-dimethyl-4-pyridinyl)-4-thiazolyl]methyl]-acetamide

Participants

Role	Name	HCID	Charge
Reactant	Acetic Anhydride	HCID 7918	—
Reactant	Triethylamine	HCID 8471	—
Reactant	[2-(cis-2,6-Dimethyl-morpholin-4-yl)-5-(2,6-dimethyl-pyridin-4-yl)-thiazol-4-yl]-methylamine	HCID 67216071	—
Solvent	Dichloromethane	HCID 6344	—
Product	N-[[2-[(2R,6S)-2,6-dimethyl-4-morpholinyl]-5-(2,6-dimethyl-4-pyridinyl)-4-thiazolyl]methyl]-acetamide	HCID 53237123	59.3%

Reaction Steps

A mixture of Intermediate 5 (150 mg, 0.45 mmol) and triethylamine (0.063 mL, 0.54 mmol) was stirred in dichloromethane (6 mL) at room temperature. Acetic acid anhydride (0.051 mL, 0.54 mmol) was added and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was washed with a potassium carbonate solution. The organic layer was dried on MgSO4, filtered, and evaporated. The residue was purified by preparative HPLC (RP Shandon Hyperprep C18 BDS—8 μm, 250 g, 5 cm; mobile phase (0.25% NH4HCO3 solution in water, MeOH+CH3CN)), yielding 100 mg (59%) of Compound 60.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08637510B2
Source dataset	uspto-grants-2014_01
ORD ID	ord-4435f6b8aee34d05a7423ccff5df4417
Source note	uspto-grants-2014_01