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

HRID 531699Notes

Reaction equation

HRID 531699 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:99]=[C:100]([F:102])[CH:101]=1)[CH2:50][N:51]1[CH:55]=[CH:54][C:53]([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]([C:77]([O:79][C:80]([CH3:83])([CH3:82])[CH3:81])=[O:78])[CH2:73][CH2:72]5)=[C:67]([NH:84][S:85]([CH3:88])(=[O:87])=[O:86])[CH:66]=4)[CH:63]=3)[N:58](S(C3C=CC(C)=CC=3)(=O)=O)[CH:57]=2)=[N:52]1.[OH-].[Li+]>C1COCC1.CO.O>[F:46][C:47]1[CH:48]=[C:49]([CH:99]=[C:100]([F:102])[CH:101]=1)[CH2:50][N:51]1[CH:55]=[CH:54][C:53]([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[CH2:72][CH2:73][N:74]([C:77]([O:79][C:80]([CH3:83])([CH3:82])[CH3:81])=[O:78])[CH2:75][CH2:76]5)=[C:67]([NH:84][S:85]([CH3:88])(=[O:87])=[O:86])[CH:66]=4)[CH:63]=3)[NH:58][CH:57]=2)=[N:52]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 118524029tert-butyl 4-(4-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(methylsulfonamido)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 136634284tert-butyl 4-(4-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(methylsulfonamido)phenyl)piperazine-1-carboxylateYield 79%

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-(3,5-difluorobenzyl)-1H-pyrazol-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(methylsulfonamido)phenyl)piperazine-1-carboxylate (55 mg, 0.067 mmol) was hydrolyzed by lithium hydroxide (9 mg, 0.201 mmol) in THF/methanol/water (2/2/1 ml) to yield 35 mg (79.0% yield) of the titled compound after preparative TLC (Silicagel-1000 micron) using 60% ethyl acetate in hexane as eluent.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-7d45ad2576be41d5897449d561900594
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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