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

HRID 531736Notes

Reaction equation

HRID 531736 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.[CH:46]1([CH2:49][C:50]([N:52]2[CH2:57][CH2:56][N:55]([C:58]3[CH:63]=[CH:62][C:61]([C:64]4[CH:65]=[C:66]5[C:72]([C:73]6[CH:74]=[N:75][N:76]([CH2:78][C:79]7[CH:84]=[CH:83][CH:82]=[C:81]([F:85])[CH:80]=7)[CH:77]=6)=[CH:71][N:70](S(C6C=CC(C)=CC=6)(=O)=O)[C:67]5=[N:68][CH:69]=4)=[CH:60][CH:59]=3)[CH2:54][CH2:53]2)=[O:51])[CH2:48][CH2:47]1.[OH-].[Li+]>C1COCC1.CO.O>[CH:46]1([CH2:49][C:50]([N:52]2[CH2:53][CH2:54][N:55]([C:58]3[CH:59]=[CH:60][C:61]([C:64]4[CH:65]=[C:66]5[C:72]([C:73]6[CH:74]=[N:75][N:76]([CH2:78][C:79]7[CH:84]=[CH:83][CH:82]=[C:81]([F:85])[CH:80]=7)[CH:77]=6)=[CH:71][NH:70][C:67]5=[N:68][CH:69]=4)=[CH:62][CH:63]=3)[CH2:56][CH2:57]2)=[O:51])[CH2:47][CH2:48]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 900301172-cyclopropyl-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)ethanoneHCID 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 900647702-cyclopropyl-1-(4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazin-1-yl)ethanoneYield 19.3%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, 2-cyclopropyl-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)ethanone (60 mg, 0.087 mmol) was hydrolyzed with lithium hydroxide (19 mg, 0.435 mmol) in THF/methanol/water (5/1/1 mL) to yield 9 mg (16.0% yield) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 8.58-8.57 (d, 1H), 8.51 (s, 1H), 8.26 (s, 1H), 7.97 (s, 1H), 7.75 (s, 1H), 7.65-7.63 (s, 2H), 7.40-7.35 (m, 1H), 7.13-7.11 (d, 3H), 7.07-7.02 (m, 2H), 6.93-6.86 (m, 1H), 6.51-6.46 (dt, 1H), 5.44 (s, 2H), 3.84-3.81 (t, 4H), 3.27 (s, 4H), 2.33-2.17 (m, 2H), 1.13-1.10 (t, 3H). MS: m/z=534.9 (M+1), HPLC: 95.19% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-22f7c1cdbae348e1b1a9a458b363ea93
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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