Dimethylamine → HCID 68161923, compound

Participants

Reaction Steps

A solution of 3-[(2S,4R)-1-acetyl-2-methyl-4-(3-pyridinylamino)-1,2,3,4-tetrahydro-6-quinolinyl]benzoic acid (for a preparation see Example 174) (9.0 mg, 0.022 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (HATU) (43.6 mg, 0.115 mmol) in N,N-dimethylformamide (DMF) (0.5 ml) was treated with N,N-diisopropylethylamine (DIPEA) (0.023 ml, 0.135 mmol) and dimethylamine (2.0M solution in THF, 0.112 ml, 0.224 mmol). The resulting mixture was stirred at room temperature for 55 min then was reduced in volume under a stream of nitrogen, diluted with acetonitrile and directly purified by MDAP to give 3-[(2S,4R)-1-acetyl-2-methyl-4-(3-pyridinylamino)-1,2,3,4-tetrahydro-6-quinolinyl]-N,N-dimethylbenzamide (5.7 mg, 0.013 mmol, 59.3% yield) as a orange gum.

Provenance & Evidence