Lithium Hydroxide → (S)-3-((4-(5-(6-(4-(2-hydroxypropyl)piperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-pyrazol-1-yl)methyl)phenol

Participants

Reaction Steps

Using similar reaction conditions as described in step-iii of example-1, (S)-3-((4-(5-(6-(4-(2-hydroxypropyl)piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-pyrazol-1-yl)methyl)phenol (180 mg, 0.271 mmol) was hydrolyzed with lithium hydroxide (34 mg, 0.813 mmol) in THF/methanol/water (2/2/0.5 mL) to yield 12 mg (9% yield) of desired product. 1H NMR (CD3OD, 400 MHz): δ 8.51-8.45 (m, 2H), 8.32-8.31 (m, 1H), 8.16 (s, 1H), 7.99-7.92 (m, 2H), 7.20-7.16 (t, 1H), 7.06-6.97 (m, 1H), 6.78-6.69 (m, 3H), 5.36 (s, 2H), 4.70-4.60 (m, 1H), 4.26-4.20 (t, 1H), 4.10-4.05 (q, 1H), 3.78-3.70 (m, 4H), 3.58-3.49 (m, 2H), 2.92-2.61 (m, 2H), 2.63-2.61 (m, 1H), 1.22-1.21 (m, 3H). MS: m/z=510.2 (M+1), HPLC: 98.41% in method A.

Provenance & Evidence