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

HRID 531635Notes

Reaction equation

HRID 531635 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.[CH3:46][O:47][C:48]1[CH:49]=[C:50]([CH:95]=[CH:96][CH:97]=1)[CH2:51][N:52]1[CH:56]=[C:55]([C:57]2[C:65]3[C:60](=[N:61][CH:62]=[C:63]([C:66]4[CH:71]=[CH:70][C:69]([CH:72]5[CH2:77][CH2:76][N:75]([C:78]([O:80][C:81]([CH3:84])([CH3:83])[CH3:82])=[O:79])[CH2:74][CH2:73]5)=[CH:68][CH:67]=4)[CH:64]=3)[N:59](S(C3C=CC(C)=CC=3)(=O)=O)[CH:58]=2)[CH:54]=[N:53]1.[OH-].[Li+]>C1COCC1.CO.O>[CH3:46][O:47][C:48]1[CH:49]=[C:50]([CH:95]=[CH:96][CH:97]=1)[CH2:51][N:52]1[CH:56]=[C:55]([C:57]2[C:65]3[C:60](=[N:61][CH:62]=[C:63]([C:66]4[CH:67]=[CH:68][C:69]([CH:72]5[CH2:77][CH2:76][N:75]([C:78]([O:80][C:81]([CH3:84])([CH3:82])[CH3:83])=[O:79])[CH2:74][CH2:73]5)=[CH:70][CH:71]=4)[CH:64]=3)[NH:59][CH:58]=2)[CH:54]=[N:53]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 1185240853-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochlorideHCID 118524086tert-butyl 4-(4-(3-(1-(3-methoxybenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate

Product 1

HCID 118523939tert-butyl 4-(4-(3-(1-(3-methoxybenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylateYield 91.4%

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-(3-methoxybenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate (120 mg, 0.167 mmol) was hydrolyzed by lithium hydroxide (70 mg, 1.67 mmol) in THF/methanol/water (12/6/3 ml) to yield crude 86 mg (91% yield) of the titled compound. MS: m/z=564.3 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-958a7d744aab40b1acc39eebd4e3e566
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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