Lithium Hydroxide → HCID 90030036, compound

HRID 531648Notes

Reaction equation

HRID 531648 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]=[CH:48][C:47]=1[CH2:52][N:53]1[CH:57]=[C:56]([C:58]2[C:66]3[C:61](=[N:62][CH:63]=[C:64]([C:67]4[CH:72]=[CH:71][C:70]([CH:73]5[CH2:78][CH2:77][N:76]([C:79]([O:81][C:82]([CH3:85])([CH3:84])[CH3:83])=[O:80])[CH2:75][CH2:74]5)=[CH:69][CH:68]=4)[CH:65]=3)[N:60](S(C3C=CC(C)=CC=3)(=O)=O)[CH:59]=2)[CH:55]=[N:54]1.[OH-].[Li+]>C1COCC1.CO.O>[N:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[CH2:52][N:53]1[CH:57]=[C:56]([C:58]2[C:66]3[C:61](=[N:62][CH:63]=[C:64]([C:67]4[CH:68]=[CH:69][C:70]([CH:73]5[CH2:74][CH2:75][N:76]([C:79]([O:81][C:82]([CH3:85])([CH3:84])[CH3:83])=[O:80])[CH2:77][CH2:78]5)=[CH:71][CH:72]=4)[CH:65]=3)[NH:60][CH:59]=2)[CH:55]=[N:54]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 118523991HCID 118523991, compoundHCID 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 90030036HCID 90030036, compoundYield 101.4%

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-2-ylmethyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate (140 mg, 0.203 mmol) was hydrolyzed by lithium hydroxide (44 mg, 1.04 mmol) in THF/methanol/water (4/4/2 ml) to yield 110 mg (98.5% yield) of the titled compound. MS: m/z=535.3 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-10a1c9dff74e400b90f299f6e4b02bfd
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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