Diisopropylethylamine → 3-(4-{6-[(5-Cyano-1,3-thiazol-2-yl)amino]pyrimidin-4-yl}piperazin-1-yl)-N-methylpyrrolidine-1-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-[(6-Chloropyrimidin-4-yl)amino]-1,3-thiazole-5-carbonitrile	HCID 11687324	—
Reactant	N-methyl-3-piperazin-1-ylpyrrolidine-1-carboxamide	HCID 21934633	—
Solvent	1-Butanol	HCID 263	—
Product	3-(4-{6-[(5-Cyano-1,3-thiazol-2-yl)amino]pyrimidin-4-yl}piperazin-1-yl)-N-methylpyrrolidine-1-carboxamide	HCID 21934679	—

Reaction Steps

35-1 (0.106 g, 0.45 mmol), 45-5 (0.095 g, 0.45 mmol) and DIEA (0.18 g, 1.79 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 45-6. Hi-Res MS: calc: 414.1819 found: 414.1827. 1H-NMR (DMSO-d6): 12.08(s, 1H); 8.42(s, 1H); 8.26(s, 1H); 6.22(s, 1H); 6.02(d, 1H); 3.55(m, 4H); 3.38 (m, 1H); 3.13(m, 1H); 2.97(m, 1H); 2.78(m, 1H); 2.50(complex, 6H); 2.45(m, 2H); 2.06(m, 1H); 1.69(m, 1H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07115597B2
Source dataset	uspto-grants-2006_10
ORD ID	ord-d924f1b7951440c18e0dfe5c5151be07
Source note	uspto-grants-2006_10