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

HRID 531862Notes

Reaction equation

HRID 531862 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:52]=[C:51]([C:53]2[CH:54]=[C:55]3[C:61]([C:62]4[C:63]([CH3:76])=[N:64][N:65]([CH2:68][C:69]5[CH:74]=[CH:73][CH:72]=[C:71]([F:75])[CH:70]=5)[C:66]=4[CH3:67])=[CH:60][N:59](S(C4C=CC(C)=CC=4)(=O)=O)[C:56]3=[N:57][CH:58]=2)[CH:50]=[CH:49][C:48]=1[CH:87]1[CH2:92][CH2:91][N:90]([C:93]([O:95][C:96]([CH3:99])([CH3:98])[CH3:97])=[O:94])[CH2:89][CH2:88]1.[OH-].[Li+]>C1COCC1.CO.O>[F:46][C:47]1[CH:52]=[C:51]([C:53]2[CH:54]=[C:55]3[C:61]([C:62]4[C:63]([CH3:76])=[N:64][N:65]([CH2:68][C:69]5[CH:74]=[CH:73][CH:72]=[C:71]([F:75])[CH:70]=5)[C:66]=4[CH3:67])=[CH:60][NH:59][C:56]3=[N:57][CH:58]=2)[CH:50]=[CH:49][C:48]=1[CH:87]1[CH2:88][CH2:89][N:90]([C:93]([O:95][C:96]([CH3:99])([CH3:98])[CH3:97])=[O:94])[CH2:91][CH2:92]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 118524018tert-butyl 4-(2-fluoro-4-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-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 90034057tert-butyl 4-(2-fluoro-4-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylateYield 69.6%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, tert-butyl 4-(2-fluoro-4-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate (200 mg, 0.265 mmol) was hydrolyzed by lithium hydroxide (56 mg, 1.329 mmol) in THF/methanol/water (5/3/1 mL) to yield 110 mg (69.6% yield) of the titled compound. MS: m/z=598.5 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-2423be98575c4ebd89171eed29d0a71b
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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