Lithium Hydroxide → 2-(dimethylamino)-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 531742Notes

Reaction equation

HRID 531742 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.[CH3:46][N:47]([CH3:95])[CH2:48][C:49]([N:51]1[CH2:56][CH2:55][N:54]([C:57]2[CH: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].[OH-].[Li+]>C1COCC1.CO.O>[CH3:46][N:47]([CH3:95])[CH2:48][C:49]([N:51]1[CH2:56][CH2:55][N:54]([C:57]2[CH:58]=[CH:59][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:61][CH:62]=2)[CH2:53][CH2:52]1)=[O:50]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 900312532-(dimethylamino)-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 900304942-(dimethylamino)-1-(4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazin-1-yl)ethanoneYield 97%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, 2-(dimethylamino)-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 (80 mg, 0.115 mmol) was hydrolyzed with lithium hydroxide (25 mg, 0.578 mmol) in THF/methanol/water (5/1/1 mL) to yield 60 mg (80.0% yield) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 8.826-8.822 (d, 1H), 8.605-8.601 (d, 1H), 8.32 (s, 1H), 8.00 (s, 1H), 7.86 (s, 1H), 7.70-7.68 (d, 2H), 7.40-7.35 (q, 1H), 7.17-7.12 (m, 3H), 7.07-7.02 (m, 2H), 5.45 (s, 2H), 4.35 (s, 2H), 3.84-3.81 (t, 2H), 3.63-3.60 (t, 2H), 3.36-3.33 (t, 4H), 2.99 (s, 6H). MS: m/z=537.9 (M+1), HPLC: 91.53% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-f76e7dd3a7bc47fda69e67e999c48f4d
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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