Lithium Hydroxide → tert-butyl 4-(4-(3-(1-(pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate

HRID 531749Notes

Reaction equation

HRID 531749 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.[N:46]1[CH:51]=[CH:50][CH:49]=[C:48]([CH2:52][N:53]2[CH:57]=[C:56]([C:58]3[C:66]4[C:61](=[N:62][CH:63]=[C:64]([C:67]5[CH:72]=[CH:71][C:70]([N:73]6[CH2:78][CH2:77][N:76]([C:79]([O:81][C:82]([CH3:85])([CH3:84])[CH3:83])=[O:80])[CH2:75][CH2:74]6)=[CH:69][CH:68]=5)[CH:65]=4)[N:60](S(C4C=CC(C)=CC=4)(=O)=O)[CH:59]=3)[CH:55]=[N:54]2)[CH:47]=1.[OH-].[Li+]>C1COCC1.CO.O>[N:46]1[CH:51]=[CH:50][CH:49]=[C:48]([CH2:52][N:53]2[CH:57]=[C:56]([C:58]3[C:66]4[C:61](=[N:62][CH:63]=[C:64]([C:67]5[CH:68]=[CH:69][C:70]([N:73]6[CH2:74][CH2:75][N:76]([C:79]([O:81][C:82]([CH3:85])([CH3:84])[CH3:83])=[O:80])[CH2:77][CH2:78]6)=[CH:71][CH:72]=5)[CH:65]=4)[NH:60][CH:59]=3)[CH:55]=[N:54]2)[CH:47]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 118523965tert-butyl 4-(4-(3-(1-(pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylateHCID 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 118524047tert-butyl 4-(4-(3-(1-(pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, tert-butyl 4-(4-(3-(1-(pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate (130 mg, 0.188 mmol) was hydrolyzed with lithium hydroxide (24 mg, 0.565 mmol) in THF/methanol/water (2/2/2 mL) to yield 100 mg (crude) of the titled compound. MS: m/z=536.7 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-d6e2222c73864030bdce512ef71358e0
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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