Trifluoroacetic acid → 2-(1-{6-[(5-Cyano-1,3-thiazol-2-yl)amino]pyrimidin-4-yl}piperidin-4-yl)-N-isopropylacetamide

Participants

Role	Name	HCID	Charge
Reactant	Trifluoroacetic acid	HCID 6422	—
Reactant	Triethylamine	HCID 8471	—
Reactant	2-[(6-Chloropyrimidin-4-yl)amino]-1,3-thiazole-5-carbonitrile	HCID 11687324	—
Reactant	Tert-butyl 4-[2-(isopropylamino)-2-oxoethyl]piperidine-1-carboxylate	HCID 21934696	—
Solvent	1-Butanol	HCID 263	—
Product	2-(1-{6-[(5-Cyano-1,3-thiazol-2-yl)amino]pyrimidin-4-yl}piperidin-4-yl)-N-isopropylacetamide	HCID 10110637	—

Reaction Steps

46-2 (0.21 g, 0.73 mmol) was treated with neat trifluoroacetic acid for 20 minutes and then the trifluoroacetic acid was evaporated off. This residue and 35-1 (0.17 g, 0.73 mmol) and triethylamine (0.37 g, 3.67 mmol) were heated at 150° C. for 3 hours in n-butanol. Upon cooling the precipitate was filtered off, washed with n-butanol and ethyl ether and then dried to afford 46-3. Hi-Res MS: calc: 386.1758 found: 386.1754. 1H-NMR (CD3OD): 8.36(s, 1H); 7.99(s, 1H); 6.14(s, 1H); 4.40(d, 2H); 3.98(m, 1H); 2.94(t, 2H); 2.10(complex, 3H); 1.77(d, 2H); 1.22(m, 2H); 1.13(d, 6H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07115597B2
Source dataset	uspto-grants-2006_10
ORD ID	ord-5ef440511e1247728e37bb969186f171
Source note	uspto-grants-2006_10