Lithium Hydroxide → 1-(4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) piperazin-1-yl)-2-hydroxyethanone

HRID 531744Notes

Reaction equation

HRID 531744 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[CH:70]=[CH:69][C:68]([N:71]5[CH2:76][CH2:75][N:74]([C:77](=[O:80])[CH2:78][OH:79])[CH2:73][CH2:72]5)=[CH:67][CH:66]=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[CH:66]=[CH:67][C:68]([N:71]5[CH2:76][CH2:75][N:74]([C:77](=[O:80])[CH2:78][OH:79])[CH2:73][CH2:72]5)=[CH:69][CH:70]=4)[CH:63]=3)[NH:58][CH:57]=2)[CH:53]=[N:52]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 900315791-(4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazin-1-yl)-2-hydroxyethanoneHCID 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 900312271-(4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) piperazin-1-yl)-2-hydroxyethanoneYield 43.5%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, 1-(4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazin-1-yl)-2-hydroxyethanone (60 mg, 0.090 mmol) was hydrolyzed with lithium hydroxide (19 mg, 0.451 mmol) in THF/methanol/water (5/1/1 mL) to yield 20 mg (35.7% yield) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 8.822-8.820 (d, 1H), 8.59 (s, 1H), 8.33 (s, 1H), 8.01 (s, 1H), 7.86 (s, 1H), 7.70-7.68 (d, 2H), 7.41-7.35 (q, 1H), 7.17-7.02 (m, 5H), 5.45 (s, 2H), 4.33 (s, 2H), 3.82-3.79 (t, 2H), 3.62 (s, 2H). MS: m/z=510.8 (M+1), HPLC: 90.93% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-d8d166c3628a4b43b1f3ad1486ec3f1d
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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