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

HRID 531740Notes

Reaction equation

HRID 531740 reaction equation
Cl.FC1C=C(C=CC=1)CN1C=C(C2C3C(=NC=C(C4C=CC(C5CCNCC5)=CC=4)C=3)N(S(C3C=CC(C)=CC=3)(=O)=O)C=2)C=N1.[F:46][C:47]1[CH:48]=[C:49]([CH:90]=[CH:91][CH:92]=1)[CH2:50][N:51]1[CH:55]=[C:54]([C:56]2[C:64]3[C:59](=[N:60][CH:61]=[C:62]([C:65]4[CH:70]=[CH:69][C:68]([N:71]5[CH2:76][CH2:75][N:74]([CH2:77][CH2:78][OH:79])[CH2:73][CH2:72]5)=[CH:67][CH:66]=4)[CH:63]=3)[N:58](S(C3C=CC(C)=CC=3)(=O)=O)[CH:57]=2)[CH:53]=[N:52]1.[OH-].[Li+]>C1COCC1.CO.O>[F:46][C:47]1[CH:48]=[C:49]([CH:90]=[CH:91][CH:92]=1)[CH2:50][N:51]1[CH:55]=[C:54]([C:56]2[C:64]3[C:59](=[N:60][CH:61]=[C:62]([C:65]4[CH:66]=[CH:67][C:68]([N:71]5[CH2:72][CH2:73][N:74]([CH2:77][CH2:78][OH:79])[CH2:75][CH2:76]5)=[CH:69][CH:70]=4)[CH:63]=3)[NH:58][CH:57]=2)[CH:53]=[N:52]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 900312692-(4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazin-1-yl)ethanolHCID 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 900308912-(4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) piperazin-1-yl)ethanolYield 87.6%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, 2-(4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazin-1-yl)ethanol (60 mg, 0.092 mmol) was hydrolyzed by lithium hydroxide (20 mg, 0.461 mmol) in THF/methanol/water (5/1/1 ml) to yield 40 mg (13.3% yield) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 8.747-8.742 (d, 2H), 8.586-8.583 (d, 1H), 8.30 (s, 1H), 7.99 (s, 1H), 7.82 (s, 1H), 7.72-7.69 (d, 2H), 7.38-7.35 (q, 1H), 7.19-7.17 (d, 2H), 7.13-7.11 (d, 1H), 7.08-7.01 (m, 2H), 5.44 (s, 2H), 3.99-3.90 (m, 5H), 3.85-3.75 (m, 2H), 3.39-3.33 (m, 3H), 3.30-3.20 (m, 2H). MS: m/z=496.9 (M+1), HPLC: 96.51% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-48c862bd6a824926ac92b7c05430e013
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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