Lithium Hydroxide → HCID 131735687, compound

HRID 531882Notes

Reaction equation

HRID 531882 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[C:48]([NH:87][C:88](=[O:94])[O:89][C:90]([CH3:93])([CH3:92])[CH3:91])=[N:49][CH:50]=[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:52]=1.[OH-].[Li+]>C1COCC1.CO.O>[F:46][C:47]1[C:48]([NH:87][C:88](=[O:94])[O:89][C:90]([CH3:92])([CH3:91])[CH3:93])=[N:49][CH:50]=[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:52]=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 131735686HCID 131735686, compound

Product 1

HCID 131735687HCID 131735687, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, tert-butyl (3-fluoro-5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)carbamate (110 mg, 0.16 mmol) was hydrolyzed by lithium hydroxide (33 mg, 0.8 mmol) in THF/methanol/water (5/5/2 mL) to yield 78 mg (91.5% yield) of the titled compound.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-8d2f4c9c85304713a2b8227923fa4465
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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