Methanol → HCID 86686984, compound

Participants

Role	Name	HCID	Charge
Reactant	Methanol	HCID 887	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2,2,2-Trichloroethyl 3-tert-butyl-1-P-tolyl-1H-pyrazol-5-ylcarbamate	HCID 9931094	—
Reactant	4-[6-((1R,4S)-4-Amino-1,2,3,4-tetrahydro-naphthalen-1-yloxy)-[1,2,4]triazolo[4,3-a]pyridin-3-ylmethyl]-piperidine-1-carboxylic acid tert-butyl ester	HCID 86686983	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 86686984	HCID 86686984	58%

Reaction Steps

A dark brown solution of (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; 162 mg, 0.401 mmol), Intermediate 22b (174 mg, 0.364 mmol) and DIPEA (0.079 mL, 0.455 mmol) in DMF (5 mL) was stirred at 100° C. for 3 h. The solution was cooled to RT, concentrated in vacuo, suspended in water (10 mL) and extracted with DCM (2×10 mL). The combined organics were passed through a hydrophobic fit and concentrated in vacuo to leave a brown gum. FCC, using 2-6% MeOH in DCM, gave the title compound as an off-white solid (155 mg, 58%). LCMS (Method 3): Rt 4.16 min, m/z 733 [MH+].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09315503B2
Source dataset	uspto-grants-2016_04
ORD ID	ord-6dd139fee926480aa1696e96cdfbfc81
Source note	uspto-grants-2016_04