Lithium Hydroxide → HCID 90064833, compound

HRID 531789Notes

Reaction equation

HRID 531789 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[N:70]=[CH:69][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)=[CH:67][CH:66]=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[N:70]=[CH:69][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)=[CH:67][CH:66]=4)[CH:63]=3)[NH:58][CH:57]=2)[CH:53]=[N:52]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 90030678HCID 90030678, 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 90064833HCID 90064833, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, (S)-1-(4-(6-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-3-yl)piperazin-1-yl) propan-2-ol (100 mg, 0.150 mmol) was hydrolyzed with lithium hydroxide (13 mg, 0.300 mmol) in THF/methanol/water (5/2/1 mL) to yield 17 mg (22.0% yield) of desired product. 1H NMR (CDCl3, 400 MHz): δ 9.01 (s, 1H), 8.879-8.874 (d, 1H), 8.60-8.59 (d, 1H), 8.42-8.41 (d, 1H), 7.88 (s, 1H), 7.78 (s, 1H), 7.69-7.67 (d, 1H), 7.742-7.41 (d, 1H), 7.34-7.29 (m, 2H), 7.07-6.96 (m, 3H), 5.39 (s, 2H), 4.00 (3.90, m 1H), 3.60-3.50 (bs, 1H), 3.36-3.32 (m, 4H), 2.95-2.90 (m, 2H), 2.70-2.60 (m, 2H), 2.50-2.30 (m, 2H), 1.19-1.18 (d, 3H). MS: m/z=512.35 (M+1), HPLC: 91.12% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-7f79e991d99f418c9d67a8d1d36c0ac3
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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