Lithium Hydroxide → 5-(6-(4-(ethylsulfonyl)piperazin-1-yl)pyridin-3-yl)-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 531810Notes

Reaction equation

HRID 531810 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.[CH2:46]([S:48]([N:51]1[CH2:56][CH2:55][N:54]([C:57]2[N:62]=[CH:61][C:60]([C:63]3[CH:64]=[C:65]4[C:71]([C:72]5[CH:73]=[N:74][N:75]([CH2:77][C:78]6[CH:83]=[CH:82][CH:81]=[C:80]([F:84])[CH:79]=6)[CH:76]=5)=[CH:70][N:69](S(C5C=CC(C)=CC=5)(=O)=O)[C:66]4=[N:67][CH:68]=3)=[CH:59][CH:58]=2)[CH2:53][CH2:52]1)(=[O:50])=[O:49])[CH3:47].[OH-].[Li+]>C1COCC1.CO.O>[CH2:46]([S:48]([N:51]1[CH2:56][CH2:55][N:54]([C:57]2[N:62]=[CH:61][C:60]([C:63]3[CH:64]=[C:65]4[C:71]([C:72]5[CH:73]=[N:74][N:75]([CH2:77][C:78]6[CH:83]=[CH:82][CH:81]=[C:80]([F:84])[CH:79]=6)[CH:76]=5)=[CH:70][NH:69][C:66]4=[N:67][CH:68]=3)=[CH:59][CH:58]=2)[CH2:53][CH2:52]1)(=[O:49])=[O:50])[CH3:47]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 1185240445-(6-(4-(ethylsulfonyl)piperazin-1-yl)pyridin-3-yl)-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 900311015-(6-(4-(ethylsulfonyl)piperazin-1-yl)pyridin-3-yl)-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridineYield 58.4%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, 5-(6-(4-(ethylsulfonyl)piperazin-1-yl)pyridin-3-yl)-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (100 mg, 0.143 mmol) was hydrolyzed with lithium hydroxide (30 mg, 0.715 mmol) in THF/methanol/water (3/2/1 mL) to yield 45 mg (58.4% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.51-8.49 (m, 2H), 8.44-8.43 (d, 2H), 8.41-8.40 (d, 1H), 8.36-8.35 (d, 1H), 8.22 (s, 1H), 7.98 (s, 1H), 7.72 (s, 1H), 7.48-7.45 (d, 1H), 7.38-7.36 (m, 1H), 7.12-7.09 (d, 1H), 7.08-6.96 (m, 2H), 5.44 (s, 2H), 3.85-3.83 (t, 4H), 3.53-3.50 (t, 4H), 3.15-3.05 (q, 2H), 1.38-1.33 (t, 3H). MS: m/z=546.1 (M+1), HPLC: 94.35% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-a41d4ae788f44a30878ff6e78f95be5f
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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