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

HRID 531797Notes

Reaction equation

HRID 531797 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:66]=[CH:67][C:68]([N:71]5[CH2:76][CH2:75][N:74]([CH2:77][C:78]#[N:79])[CH2:73][CH2:72]5)=[N:69][CH:70]=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][C:78]#[N:79])[CH2:75][CH2:76]5)=[N:69][CH:70]=4)[CH:63]=3)[NH:58][CH:57]=2)[CH:53]=[N:52]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 900315082-(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl) acetonitrileHCID 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 729447532-(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)acetonitrileYield 33.3%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, 2-(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl) acetonitrile (60 mg, 0.092 mmol) was hydrolyzed by lithium hydroxide (8 mg, 0.185 mmol) in THF/methanol/water (5/1/1 ml) to yield 15 mg (33.3% yield) of the titled compound. 1H NMR (CDCl3, 400 MHz): δ 9.19 (s, 1H), 8.50-8.47 (dd, 2H), 8.128-8.123 (d, 1H), 7.86 (s, 1H), 7.79-7.76 (dd, 1H), 7.70 (s, 1H), 7.447-7.441 (d, 1H), 7.35-7.30 (m, 1H), 7.10-6.90 (m, 3H), 6.80-6.78 (d, 1H), 5.39 (s, 2H), 3.70-3.67 (t, 4H), 3.61 (s, 2H), 2.76-2.74 (t, 4H). MS: m/z=493.4 (M+1), HPLC: 97.07% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-a35c80e5746943308b4b4b58b2f600a7
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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