Lithium Hydroxide → (S)-1-(4-(5-(3-(1-phenethyl-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-phenethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)propan-2-ol	HCID 118524061	—
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-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl) piperazin-1-yl)propan-2-ol	HCID 90030958	83.3%

Reaction Steps

Using similar reaction conditions as described in step-iii of example-1, (S)-1-(4-(5-(3-(1-phenethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)propan-2-ol (80 mg, 0.12 mmol) was hydrolyzed with lithium hydroxide (25 mg, 0.6 mmol) in THF/methanol/water (2/2/1 mL) to yield 50 mg (83.3% yield) of desired product. 1H NMR (CD3OD, 300 MHz): δ 8.53-8.52 (d, 2H), 8.36-8.35 (d, 1H), 8.12-8.08 (dd, 1H), 7.896-7.893 (d, 1H), 7.818-7.816 (d, 1H), 7.67 (s, 1H), 7.26-7.20 (m, 3H), 7.17-7.12 (m, 3H), 4.47-4.43 (d, 2H), 4.30-4.20 (t, 1H), 3.60-3.40 (bs, 4H), 3.25-3.10 (m, 4H), 1.27-1.25 (d, 3H). MS: m/z=408.6 (M+1), HPLC: 93.50% in method A.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09353107B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-29be7f2ec00645e886b0e648f47b13a3
Source note	uspto-grants-2016_05