L-Prolinol → 3-(3,4-difluorophenyl)-N-((S)-1-((S)-2-(hydroxymethyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)-6,7-dihydropyrano[4,3-c]pyrazole-1(4H)-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	L-Prolinol	HCID 640091	—
Reactant	(S)-N-(1-(2-cyanoethylamino)-3,3-dimethyl-1-oxobutan-2-yl)-3-(3,4-difluorophenyl)-6,7-dihydropyrano[4,3-c]pyrazole-1(4H)-carboxamide	HCID 46862252	—
Product	3-(3,4-difluorophenyl)-N-((S)-1-((S)-2-(hydroxymethyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)-6,7-dihydropyrano[4,3-c]pyrazole-1(4H)-carboxamide	HCID 58504334	—

Reaction Steps

Compound 109 was prepared by the procedure described for the synthesis of compound 104 by replacing 2-cyanoethylamine with L-prolinol. LCMS (+ESI) m/z=477.3 [M+H]+. 1H NMR (CDCl3) δ 7.88 (d, J=9.7 Hz, 1H), 7.45-7.51 (m, 1H), 7.30-7.32 (m, 1H), 7.19-7.26 (m, 1H), 4.82 (s, 2H), 4.64 (d, J=9.8 Hz, 1H), 4.45 (br, 1H), 4.29-4.33 (m, 1H), 3.91-3.97 (m, 3H), 3.55-3.74 (m, 3H), 3.18 (br, 2H), 1.86-2.11 (m, 3H), 1.59-1.66 (m, 1H), 1.11 (s, 9H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08653127B2
Source dataset	uspto-grants-2014_02
ORD ID	ord-dc7dfaa83ca94fa4aa21af5aa1f0e7df
Source note	uspto-grants-2014_02