1,2-Diaminocyclohexane → HCID 178519088, compound

Participants

Role	Name	HCID	Charge
Reactant	1,2-Diaminocyclohexane	HCID 4610	—
Reactant	Thionyl Chloride	HCID 24386	—
Reactant	Cesium fluoride	HCID 25953	—
Reactant	4-Bromobenzene-1,2-diamine	HCID 323593	—
Reactant	Phosphine, triphenyl-, hydrobromide	HCID 517696	—
Reactant	Tert-Butyl hypochlorite	HCID 521297	—
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	HCID 57488485	HCID 57488485	—
Reactant	Butyllithium	HCID 178418339	—
Catalyst	Copper iodide	HCID 83717	—
Solvent	Formic Acid	HCID 284	—
Product	HCID 178519088	HCID 178519088	—

Reaction Steps

The compound was synthesized according to method 5 starting from n-butyl lithium (2.3M in hexane; 3.66 mL, 7.32 mmol), tri phenyl phosphonium bromide (2.6 g, 7.32 mmol), 4-(4-morpholinocyclohexyl)benzaldehyde (1 g, 3.66 mmol), t-butyl hypochlorite (1.13 mL, 8.85 mmol), Boc carbamate (1.03 g, 8.85 mmol) 0.4M aqueous sodium hydroxide (360 mg in 10 mL), (DHQ)2PHAL (114 mg, mmol), potassium osmate dihydrate (40 mg, 0.12 mmol), thionyl chloride (0.6 mL, 8 mmol), 1,2-diamino-4-bromobenzene (160 mg, 0.84 mmol) and cesium fluoride (190 mg, 1.26 mmol), copper iodide (25 mg, 0.13 mmol) and 1,2-diaminocyclohexane (15 mg, 0.13 mmol), formic acid (10 mL). Yield: 40 mg (2.4%), MS m/z 447.4 (M+H)+; 1H-NMR (400 MHz, DMSO-d6): δ 12.38 (s, 1H); 8.15 (s, 1H); 7.60-7.16 (m, 6H); 5.69 (t, 1H); 4.8 (t, 1H); 4.13-4.10 (q, 1H); 3.57 (t, 4H); 2.56 (merged with DMSO, 1H); 2.33 (s, 4H); 2.11 (s, 1H); 1.91-1.67 (m, 5H); 1.45-1.38 (m, 4H), HPLC (λ=214 nm, [A]: rt 7.95 min (97.87%)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09173885B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-d798076a06cc4d3f9165ab75b2a65f3d
Source note	uspto-grants-2015_11