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

HRID 531812Notes

Reaction equation

HRID 531812 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([C:49]([N:51]2[CH2:56][CH2:55][N:54]([C:57]3[CH:62]=[CH:61][C:60]([C:63]4[CH:64]=[C:65]5[C:71]([C:72]6[CH:73]=[N:74][N:75]([CH2:77][C:78]7[CH:83]=[CH:82][CH:81]=[C:80]([F:84])[CH:79]=7)[CH:76]=6)=[CH:70][N:69](S(C6C=CC(C)=CC=6)(=O)=O)[C:66]5=[N:67][CH:68]=4)=[CH:59][N:58]=3)[CH2:53][CH2:52]2)=[O:50])[CH2:48][CH2:47]1.[OH-].[Li+]>C1COCC1.CO.O>[CH:46]1([C:49]([N:51]2[CH2:56][CH2:55][N:54]([C:57]3[CH:62]=[CH:61][C:60]([C:63]4[CH:64]=[C:65]5[C:71]([C:72]6[CH:73]=[N:74][N:75]([CH2:77][C:78]7[CH:83]=[CH:82][CH:81]=[C:80]([F:84])[CH:79]=7)[CH:76]=6)=[CH:70][NH:69][C:66]5=[N:67][CH:68]=4)=[CH:59][N:58]=3)[CH2:53][CH2:52]2)=[O:50])[CH2:48][CH2:47]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 90031347cyclopropyl(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)methanoneHCID 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 72944756cyclopropyl(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)methanoneYield 54.5%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, cyclopropyl(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)methanone (100 mg, 0.148 mmol) was hydrolyzed with lithium hydroxide (31 mg, 0.74 mmol) in THF/methanol/water (3/2/1 mL) to yield 42 mg (54.5% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.53 (s, 2H), 8.49-8.48 (d, 1H), 8.46-8.45 (d, 1H), 8.24 (s, 1H), 7.998-7.995 (d, 1H), 7.74 (s, 1H), 7.50-7.47 (d, 1H), 7.37-7.35 (m, 1H), 7.12-6.98 (m, 3H), 5.44 (s, 2H), 4.08-3.83 (m, 8H), 2.05-1.95 (m, 1H), 0.95-0.87 (m, 2H). MS: m/z=522.4 (M+1), HPLC: 96.90% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-0e2c68da487541c4aa4054bdb05efa8e
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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