1,2-Diaminocyclohexane → HCID 178519151, compound

Participants

Role	Name	HCID	Charge
Reactant	1,2-Diaminocyclohexane	HCID 4610	—
Reactant	Hexane	HCID 8058	—
Reactant	Thionyl Chloride	HCID 24386	—
Reactant	Cesium fluoride	HCID 25953	—
Reactant	Formamidine acetate	HCID 160693	—
Reactant	4-Bromobenzene-1,2-diamine	HCID 323593	—
Reactant	Tert-Butyl hypochlorite	HCID 521297	—
Reactant	HCID 21713226	HCID 21713226	—
Reactant	HCID 21983788	HCID 21983788	—
Reactant	1-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazine	HCID 51003674	—
Reactant	Butyllithium	HCID 178418339	—
Catalyst	Copper iodide	HCID 83717	—
Product	HCID 178519151	HCID 178519151	—

Reaction Steps

The compound was further synthesized according to method 5 starting from the product of step C (1.6 g, 7.96 mmol), 2.3M n-butyl lithium in hexane (6.19 mL, 14.92 mmol), triphenyl phosphonium methyl bromide (6.68 g, 15.92 mmol), T-butyl hypochloride (2 mL, 18.85 mmol), Boc carbamate (2.17 g, 18.60 mmol), (DHQ)2PHAL (240 mg, 0.309 mmol), potassium osmate dihydrate (90 mg, 0.247 mmol), Thionyl chloride (0.439 mL, 6.024 mmol), 4-bromo-1,2-diamino benzene (130 mg, 0.697 mmol), cesium fluoride (212 mg, 1.395 mmoles) and copper iodide (20 mg, 0.104 mmoles), 1,2-diaminocyclohexane (1 mL), formamidine acetate (23 mg, 0.219 mmoles). Yield: 0.03 g (0.6%). MS m/z 375.3 (M+H)+; 1H-NMR 400 MHz, CDCl3): δ 7.94 (s, 1H); 7.67 (s, 1H); 7.52 (s, 1H); 7.15 (d, 3H); 6.96 (d, 2H); 5.34 (q, 1H); 4.77 (t, 1H); 4.27 (q, 1H); 2.40-2.38 (t, 1H); 0.88-0.80 (m, 4H); 0.64-0.63 (m, 4H); HPLC (λ=214 nm, [A]: rt 14.39 min (95%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09173885B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-ddb2b75b93ba40f8b288fe7c52c5f2a3
Source note	uspto-grants-2015_11