Lithium Hydroxide → (S)-1-(4-(5-(3-(1-(3-fluorobenzyl)-5-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)propan-2-ol

Participants

Role	Name	HCID	Charge
Reactant	Lithium Hydroxide	HCID 3939	—
Reactant	(S)-1-(4-(5-(3-(1-(3-fluorobenzyl)-5-methyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)propan-2-ol	HCID 118523929	—
Reactant	3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochloride	HCID 118524085	—
Solvent	Methanol tetrahydrofuran water	HCID 21892291	—
Product	(S)-1-(4-(5-(3-(1-(3-fluorobenzyl)-5-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)propan-2-ol	HCID 72944955	11%

Reaction Steps

Using similar reaction conditions as described in step-iii of example-1, (S)-1-(4-(5-(3-(1-(3-fluorobenzyl)-5-methyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl) piperazin-1-yl)propan-2-ol (350 mg, 0.51 mmol) was hydrolyzed with lithium hydroxide (65 mg, 1.54 mmol) in THF/methanol/water (6/4/2 mL) to yield 40 mg (11% yield) after purification by preparative HPLC as a mixture of two isomers. MS: m/z=526.5 (M+1). HPLC: 89.1% in method B.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09353107B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-6a80d6f9bcda4d899b835e42665ecbc6
Source note	uspto-grants-2016_05