Ammonia → HCID 86687018, compound

Participants

Role	Name	HCID	Charge
Reactant	Ammonia	HCID 222	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2,2,2-Trichloroethyl 3-tert-butyl-1-P-tolyl-1H-pyrazol-5-ylcarbamate	HCID 9931094	—
Reactant	(1S,4R)-4-[3-((R)-3-Triisopropylsilanyloxy-pyrrolidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-ylamine	HCID 86687019	—
Solvent	Methanol	HCID 887	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 86687018	HCID 86687018	53%

Reaction Steps

A solution of Intermediate 38c (100 mg, 0.191 mmol), (5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester (Synthetic Communications, 2009, 39, 3999-4009, which is incorporated herein by reference in its entirety; 115 mg, 0.286 mmol) and DIPEA (100 mg, 0.764 mmol) in DMF (2 mL) was stirred at 60° C. for 1 h. The reaction mixture was applied to an SCX-2 cartridge (10 g) and washed with MeOH. The product was eluted with 2M NH3 in MeOH; concentration in vacuo gave a residue. FCC, using 0-10% [2M NH3 in MeOH] in DCM, gave the title compound as a viscous yellow oil (80 mg, 53%). LCMS (Method 4): Rt 4.55 min, m/z 777 [MH+].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09315503B2
Source dataset	uspto-grants-2016_04
ORD ID	ord-cbe1909ff4714bcdb6f660195ac7333d
Source note	uspto-grants-2016_04