Lithium Hydroxide → (S)-1-(4-(5-(3-(1-(3-methylbenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)propan-2-ol

HRID 531785Notes

Reaction equation

HRID 531785 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][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]=[CH:67][C:68]([N:71]5[CH2:76][CH2:75][N:74]([CH2:77][C@@H:78]([OH:80])[CH3:79])[CH2:73][CH2:72]5)=[N: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>[CH3:46][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]=[CH:67][C:68]([N:71]5[CH2:76][CH2:75][N:74]([CH2:77][C@@H:78]([OH:80])[CH3:79])[CH2:73][CH2:72]5)=[N:69][CH:70]=4)[CH:63]=3)[NH:58][CH:57]=2)[CH:53]=[N:52]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 90031155(S)-1-(4-(5-(3-(1-(3-methylbenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl) propan-2-olHCID 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 90030693(S)-1-(4-(5-(3-(1-(3-methylbenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)propan-2-olYield 32.6%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, (S)-1-(4-(5-(3-(1-(3-methylbenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl) propan-2-ol (100 mg, 0.151 mmol) was hydrolyzed with lithium hydroxide (19 mg, 0.453 mmol) in THF/methanol/water (2/2/0.5 mL) to yield 25 mg (21% yield) of desired product. 1H NMR (CD3OD, 400 MHz): δ 8.559-8.553 (d, 1H), 8.479-8.474 (d, 1H), 8.425-8.420 (d, 1H), 8.17 (s, 1H), 8.08-8.06 (dd, 1H), 7.94 (s, 1H), 7.69 (s, 1H), 7.28-7.22 (t, 1H), 7.15-7.10 (m, 4H), 5.39 (s, 2H), 4.25-4.32 (m, 1H), 3.10-3.30 (m, 2H), 2.34 (s, 3H), 1.28-1.27 (d, 3H). MS: m/z=508.2 (M+1), HPLC: 98.90% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-62d19b34d0f84abfaffe8eb8b8a23e9c
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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