Lithium Hydroxide → HCID 72944754, compound

HRID 531802Notes

Reaction equation

HRID 531802 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.[F:46][C:47]1[CH:48]=[C:49]([CH:91]=[CH:92][CH:93]=1)[CH2:50][N:51]1[CH:55]=[C:54]([C:56]2[C:64]3[C:59](=[N:60][CH:61]=[C:62]([C:65]4[CH:66]=[N:67][C:68]([N:71]5[CH2:76][CH2:75][N:74]([CH2:77][CH:78]([CH3:80])[CH3:79])[CH2:73][CH2:72]5)=[CH:69][CH:70]=4)[CH:63]=3)[N:58](S(C3C=CC(C)=CC=3)(=O)=O)[CH:57]=2)[CH:53]=[N:52]1.[OH-].[Li+]>C1COCC1.CO.O>[F:46][C:47]1[CH:48]=[C:49]([CH:91]=[CH:92][CH:93]=1)[CH2:50][N:51]1[CH:55]=[C:54]([C:56]2[C:64]3[C:59](=[N:60][CH:61]=[C:62]([C:65]4[CH:66]=[N:67][C:68]([N:71]5[CH2:72][CH2:73][N:74]([CH2:77][CH:78]([CH3:79])[CH3:80])[CH2:75][CH2:76]5)=[CH:69][CH:70]=4)[CH:63]=3)[NH:58][CH:57]=2)[CH:53]=[N:52]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 90030662HCID 90030662, compoundHCID 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 72944754HCID 72944754, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(4-isobutylpiperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (70 mg, 0.105 mmol) was hydrolyzed by lithium hydroxide (27 mg, 0.632 mmol) in THF/methanol/water (3/2/1 ml) to yield 8 mg (15.0% yield) of the titled compound. 1H NMR (CDCl3, 300 MHz): δ 8.83 (s, 1H), 8.49-8.45 (dd, 2H), 8.11-8.10 (d, 1H), 7.85 (s, 1H), 7.76-7.69 (m, 2H), 7.42-7.41 (d, 1H), 7.39-7.30 (m, 1H), 7.10-6.90 (m, 3H), 6.77-6.74 (d, 1H), 5.38 (s, 2H), 3.60-3.59 (t, 4H), 2.60-2.50 (t, 4H), 2.16-2.14 (d, 2H), 1.90-1.80 (m, 1H), 0.95-0.93 (d, 6H). MS: m/z=510.3 (M+1), HPLC: 93.26% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-588f7171157344798a2e18c69dbbe010
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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