Cesium carbonate → (S)-1-{5-tert-Butyl-3-[2-(7-nitro-benzo[1,2,5]oxadiazol-4-ylamino)-pyridin-3-ylmethyl]-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl}-pyrrolidin-3-ol

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	4-Amino-7-nitrobenzofurazan	HCID 601894	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	(S)-1-[5-tert-Butyl-3-(2-chloro-pyridin-3-ylmethyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidin-3-ol	HCID 86295836	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	(S)-1-{5-tert-Butyl-3-[2-(7-nitro-benzo[1,2,5]oxadiazol-4-ylamino)-pyridin-3-ylmethyl]-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl}-pyrrolidin-3-ol	HCID 86683341	16.5%

Reaction Conditions

Temperature	120 °C

Reaction Steps

A mixture of (S)-1-[5-tert-Butyl-3-(2-chloro-pyridin-3-ylmethyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidin-3-ol (example 140) (5.30 mg, 13.7 μmol), 7-nitrobenzo[c][1,2,5]oxadiazol-4-amine (2.95 mg, 16.4 μmol), Pd2(dba)3 (1.25 mg, 1.37 μmol), xantphos (2.15 mg, 3.71 μmol) and Cs2CO3 (8.06 mg, 24.8 μmol) in dioxane (500 μl) was heated to 120° C. and stirred for 20 min. The crude material was filtered (celite), concentrated and purified by preparative HPLC eluting with a gradient formed from acetonitrile, water and NEt3. The product containing fractions were evaporated to yield 1.2 mg (16%) of the title compound as red solid. MS(m/e): 532.4 (MH+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09056866B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-32798b543ce94260b7bbd77c13db3057
Source note	uspto-grants-2015_06