Lithium Hydroxide → 5-(3-fluoro-4-(1-methylpiperidin-4-yl)phenyl)-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

HRID 531850Notes

Reaction equation

HRID 531850 reaction equation
Cl.F[C:3]1C=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]([C:59]2[CH:60]=[C:61]3[C:67]([C:68]4[CH:69]=[N:70][N:71]([CH2:73][C:74]5[CH:79]=[CH:78][CH:77]=[C:76]([F:80])[CH:75]=5)[CH:72]=4)=[CH:66][N:65]([S:81]([C:84]4[CH:90]=[CH:89][C:87]([CH3:88])=[CH:86][CH:85]=4)(=[O:83])=[O:82])[C:62]3=[N:63][CH:64]=2)[CH:50]=[CH:51][C:52]=1[CH:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1.[OH-].[Li+]>C1COCC1.CO.O>[F:46][C:47]1[CH:48]=[C:49]([C:59]2[CH:60]=[C:61]3[C:67]([C:68]4[CH:69]=[N:70][N:71]([CH2:73][C:74]5[CH:79]=[CH:78][CH:77]=[C:76]([F:80])[CH:75]=5)[CH:72]=4)=[CH:66][N:65]([S:81]([C:84]4[CH:85]=[CH:86][C:87]([CH3:88])=[CH:89][CH:90]=4)(=[O:83])=[O:82])[C:62]3=[N:63][CH:64]=2)[CH:50]=[CH:51][C:52]=1[CH:53]1[CH2:54][CH2:55][N:56]([CH3:3])[CH2:57][CH2:58]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 900337135-(3-fluoro-4-(piperidin-4-yl)phenyl)-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 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 1185239535-(3-fluoro-4-(1-methylpiperidin-4-yl)phenyl)-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineYield 20.7%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, 5-(3-fluoro-4-(piperidin-4-yl)phenyl)-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (88 mg, 0.138 mmol) was hydrolyzed with lithium hydroxide (58 mg, 1.381 mmol) in THF/methanol/water (12/4/4 mL) to yield 17 mg (20.7% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.68-8.67 (d, 1H), 8.60 (s, 1H), 8.29 (s, 1H), 7.98 (s, 1H), 7.79 (s, 1H), 7.60-7.30 (m, 4H), 7.13-7.00 (m, 3H), 5.44 (s, 2H), 3.70-3.50 (m, 2H), 3.30-3.10 (m, 3H), 2.93 (s, 3H), 2.16-2.02 (m, 4H). MS: m/z=484.4 (M+1), HPLC: 97.49% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-57519876d8d7481587de4958d769289a
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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