Dichloromethane → Dichloromethane methanol ammonium hydroxide

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Trifluoroacetic acid	HCID 6422	—
Reactant	N-(3-ethyl-1-((1-((3R,4R)-3-fluoropiperidin-4-yl)-1H-pyrazol-4-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide	HCID 67259695	—
Reactant	(3R,4R)-tert-butyl 4-(4-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)-1H-pyrazol-1-yl)-3-fluoropiperidine-1-carboxylate	HCID 70814963	—
Product	Dichloromethane methanol ammonium hydroxide	HCID 21896990	—
Product	N-(3-ethyl-1-((1-((3R,4R)-3-fluoropiperidin-4-yl)-1H-pyrazol-4-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide	HCID 67259695	—

Reaction Steps

Preparation of N-(3-ethyl-1-((1-((3R,4R)-3-fluoropiperidin-4-yl)-1H-pyrazol-4-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide]: To (3R,4R)-tert-butyl 4-(4-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)-1H-pyrazol-1-yl)-3-fluoropiperidine-1-carboxylate (7 mg, 0.01 mmol) in DCM (2 mL) was added TFA (1 mL). The reaction mixture was stirred for 30 minutes, concentrated and silica gel chromatography (DCM/MeOH/NH4OH 10:1:0.1) gave the final product (3 mg). MS (ES+APCI) m/z=487 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08841455B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-278158b939ea421c9214b502ed029f5d
Source note	uspto-grants-2014_09