Lithium Hydroxide → HCID 90030666, compound

HRID 531730Notes

Reaction equation

HRID 531730 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:88]=[CH:89][CH:90]=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:70]=[CH:69][C:68]([N:71]5[CH2:76][CH2:75][CH:74]([OH:77])[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:88]=[CH:89][CH:90]=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][CH:74]([OH:77])[CH2:73][CH2:72]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 90031406HCID 90031406, 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 90030666HCID 90030666, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, 1-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidin-4-ol (130 mg, 0.209 mmol) was hydrolyzed with lithium hydroxide (28 mg, 0.62 mmol) in THF/methanol/water (3/3/1 mL) to yield 35 mg (28.7% yield) of desired product. 1H NMR (CD3OD, 300 MHz): δ 8.56 (s, 2H), 8.24 (s, 1H), 7.97-7.94 (m, 3H), 7.74-7.70 (m, 3H), 7.38-7.35 (m, 1H), 7.12-6.99 (m, 3H), 4.10-4.08 (m, 1H), 3.90-3.84 (m, 2H), 3.64-3.57 (m, 2H), 2.27-2.20 (m, 2H), 2.04-1.97 (m, 2H). MS: m/z=468.4 (M+1), HPLC: 91.74% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-46adc2612f5240cabd322d747aa3df3b
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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