Lithium Hydroxide → HCID 90030752, compound

HRID 531828Notes

Reaction equation

HRID 531828 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:91]=[CH:92][CH:93]=1)[CH2:50][N:51]1[CH:55]=[C:54]([C:56]2[C:64]3[C:59](=[N:60][CH:61]=[C:62]([C:65]4[N:66]=[CH:67][C:68]([N:71]5[CH2:76][CH2:75][N:74]([CH2:77][C@@H:78]([OH:80])[CH3:79])[CH2:73][CH2:72]5)=[N:69][CH:70]=4)[CH:63]=3)[N:58](S(C3C=CC(C)=CC=3)(=O)=O)[CH:57]=2)[CH:53]=[N:52]1.[OH-].[Li+]>C1COCC1.CO.O>[F:46][C:47]1[CH:48]=[C:49]([CH:91]=[CH:92][CH:93]=1)[CH2:50][N:51]1[CH:55]=[C:54]([C:56]2[C:64]3[C:59](=[N:60][CH:61]=[C:62]([C:65]4[N:66]=[CH:67][C:68]([N:71]5[CH2:72][CH2:73][N:74]([CH2:77][C@@H:78]([OH:80])[CH3:79])[CH2:75][CH2:76]5)=[N:69][CH:70]=4)[CH:63]=3)[NH:58][CH:57]=2)[CH:53]=[N:52]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 90030155HCID 90030155, 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 90030752HCID 90030752, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, (S)-1-(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyrazin-2-yl)piperazin-1-yl) propan-2-ol (230 mg, 0.34 mmol) was hydrolyzed with lithium hydroxide (44 mg, 1.03 mmol) in THF/methanol/water (4/4/2 mL) to yield 40 mg (18.5% yield) of desired product. 1H NMR (CD3OD, 300 MHz): δ 8.83-8.75 (m, 3H), 8.44-8.43 (d, 1H), 8.22 (s, 1H), 7.972-7.970 (d, 1H), 7.68 (s, 1H), 7.44-7.32 (m, 1H), 7.16-6.96 (m, 3H), 5.44 (s, 2H), 4.70-4.45 (m, 3H), 4.30-4.10 (m, 2H), 3.80-3.60 (m, 2H), 3.60-3.30 (m, 4H), 1.27-1.25 (d, 3H). MS: m/z=513.3 (M+1), HPLC: 97.55% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-22d85ed893d745af89e18faa371753cc
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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