3-Bromopyridine → 5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-N-[(3S)-1-(pyridazin-4-yl)pyrrolidin-3-yl]thiophene-2-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	3-Bromopyridine	HCID 12286	—
Reactant	Tert-butyl 4-(4-(azetidine-3-carboxamido)phenoxy)piperidine-1-carboxylate	HCID 86702036	—
Reactant	(S)-5-(1-isobutyl-1H-pyrazol-4-yl)-N-(pyrrolidin-3-yl)thiophene-2-carboxamide	HCID 86702056	—
Product	5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-N-[(3S)-1-(pyridazin-4-yl)pyrrolidin-3-yl]thiophene-2-carboxamide	HCID 86702055	—

Reaction Steps

The title compound was prepared as described in Example 1C, substituting 4-bromopyridazine for 3-bromopyridine and (S)-5-(1-isobutyl-1H-pyrazol-4-yl)-N-(pyrrolidin-3-yl)thiophene-2-carboxamide for tert-butyl 4-(4-(azetidine-3-carboxamido)phenoxy)piperidine-1-carboxylate. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.75-0.98 (m, 6 H) 1.98-2.44 (m, 3 H) 3.67-4.18 (m, 6 H) 4.66 (s, 1 H) 7.15 (dd, J=7.12, 3.05 Hz, 1 H) 7.21 (d, J=3.73 Hz, 1 H) 7.54-7.91 (m, 2 H) 8.14 (s, 1 H) 8.56-8.95 (m, 3 H); MS (ESI(+)) m/e 397 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08975398B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-b55fc0df0fd643158012426905ce62c1
Source note	uspto-grants-2015_03