Lithium Hydroxide → 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine

HRID 531622Notes

Reaction equation

HRID 531622 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:43]=[CH:44][CH:45]=1)[CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([CH:27]5[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]5)=[CH:23][CH:22]=4)[CH:19]=3)[N:14](S(C3C=CC(C)=CC=3)(=O)=O)[CH:13]=2)[CH:9]=[N:8]1.FC1C=C(C=CC=1)CN1C=C(C2C3C(=NC=C(C4C=CC(C5CCN(C[C@@H](O)C)CC5)=CC=4)C=3)N(S(C3C=CC(C)=CC=3)(=O)=O)C=2)C=N1.[OH-].[Li+]>C1COCC1.CO.O>[F:2][C:3]1[CH:4]=[C:5]([CH:43]=[CH:44][CH:45]=1)[CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[CH:23][C:24]([CH:27]5[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]5)=[CH:25][CH:26]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH:9]=[N:8]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 90030588(S)-1-(4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidin-1-yl)propan-2-olHCID 1185240853-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochloride

Product 1

HCID 900305953-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1H-pyrrolo[2,3-b]pyridineYield 5%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, (S)-1-(4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidin-1-yl)propan-2-ol (127 mg, 0.191 mmol) was hydrolyzed by lithium hydroxide (80 mg, 1.913 mmol) in THF/methanol/water (20/10/5 ml) to yield 15 mg (5% yield) of the titled. 1H NMR (CD3OD, 400 MHz): δ 7.46-8.45 (d, 1H), 8.33-8.32 (d, 1H), 8.19 (s, 1H), 7.93 (s, 1H), 7.63-7.61 (m, 3H), 7.39-7.34 (m, 3H), 7.11-7.09 (d, 1H), 7.06-7.01 (m, 2H), 5.43 (s, 2H), 4.05-4.00 (m, 1H), 3.25-3.19 (t, 2H), 2.64-2.33 (m, 4H), 1.93-1.85 (m, 4H), 1.30-1.26 (m, 1H), 1.20-1.18 (d, 3H). MS: m/z=510.2 (M+1), HPLC: 96.39% in method A.

Workup

  1. customreaction conditions
  2. customto yield 15 mg (5% yield) of the

Sources & evidence

ORD record
ord-b639f2eb0832497b8cc99dd4cacbc74b
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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