N,N-Dimethylglycine → HCID 10412210, compound

Participants

Role	Name	HCID	Charge
Reactant	N,N-Dimethylglycine	HCID 673	—
Reactant	Triethylamine	HCID 8471	—
Reactant	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
Reactant	8-Chloro-1-(3,4,5,6-tetrahydro-2h-[1,2']bipyridinyl-4-yl)-5,6-dihydro4h-2,3,5,10b-tetraaza-benzo[e]azulene	HCID 11326488	—
Solvent	Dimethylacetamide	HCID 31374	—
Product	HCID 10412210	HCID 10412210	57.8%

Reaction Conditions

Temperature	50 °C

Reaction Steps

A solution of HBTU (152 mg, 0.38 mmol) in N,N-dimethylacetamide (1.9 ml) was added to a solution of the amine of example 4 (97 mg, 0.26 mmol), triethylamine (1.5 μl, cat.) and dimethylamino-acetic acid (36 mg, 0.26 mmol) in N,N-dimethylacetamide (2.5 ml) and heated to 50° C. for 2 hours. The mixture was cooled and the solvent evaporated under reduced pressure. The residue was partitioned between dichloromethane (10 ml) and 2M aqueous sodium hydroxide solution (10 ml). The organic phase was dried over magnesium sulphate before being evaporated under reduced pressure and purified by chromatography on silica gel using methanol and ammonium hydroxide in dichloromethane (7:1:93) as eluant to afford the title compound (70 mg) as a brown foam.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07442795B2
Source dataset	uspto-grants-2008_10
ORD ID	ord-aba9146165df47409edd324aff5f85fd
Source note	uspto-grants-2008_10