Lithium Hydroxide → 3-(1-phenethyl-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 531771Notes

Reaction equation

HRID 531771 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.[CH2:46]([N:54]1[CH:58]=[C:57]([C:59]2[C:67]3[C:62](=[N:63][CH:64]=[C:65]([C:68]4[CH:69]=[N:70][C:71]([N:74]5[CH2:79][CH2:78][NH:77][CH2:76][CH2:75]5)=[CH:72][CH:73]=4)[CH:66]=3)[N:61](S(C3C=CC(C)=CC=3)(=O)=O)[CH:60]=2)[CH:56]=[N:55]1)[CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.[OH-].[Li+]>C1COCC1.CO.O>[CH2:46]([N:54]1[CH:58]=[C:57]([C:59]2[C:67]3[C:62](=[N:63][CH:64]=[C:65]([C:68]4[CH:69]=[N:70][C:71]([N:74]5[CH2:75][CH2:76][NH:77][CH2:78][CH2:79]5)=[CH:72][CH:73]=4)[CH:66]=3)[NH:61][CH:60]=2)[CH:56]=[N:55]1)[CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 900313493-(1-phenethyl-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 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 900311753-(1-phenethyl-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridineYield 100%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, 3-(1-phenethyl-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (55 mg, 0.09 mmol) was hydrolyzed with lithium hydroxide (20 mg, 0.45 mmol) in THF/methanol/water (2/1/1 mL) to yield 40 mg (100% yield) of desired product. 1H NMR (CD3OD, 300 MHz): δ 8.51-8.50 (d, 1H), 8.43 (s, 1H), 8.25-8.15 (dd, 1H), 7.91-7.86 (d, 2H), 7.68 (s, 1H), 7.27-7.21 (m, 3H), 7.14-7.12 (m, 3H), 4.50-4.40 (t, 2H), 3.97-3.94 (t, 4H), 3.43-3.34 (t, 4H), 3.20-3.18 (t, 2H). MS: m/z=450.4 (M+1), HPLC: 92.83% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-c991f6d4506f4a1cad5e5f6730de0673
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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