Lithium Hydroxide → HCID 90030763, compound

HRID 531690Notes

Reaction equation

HRID 531690 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:96]=[CH:97][CH:98]=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][N:74]([CH2:77][C:78]([NH2:80])=[O:79])[CH2:73][CH2:72]5)=[C:67]([NH:81][S:82]([CH3:85])(=[O:84])=[O:83])[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:96]=[CH:97][CH:98]=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[CH2:72][CH2:73][N:74]([CH2:77][C:78]([NH2:80])=[O:79])[CH2:75][CH2:76]5)=[C:67]([NH:81][S:82]([CH3:85])(=[O:83])=[O:84])[CH:66]=4)[CH:63]=3)[NH:58][CH:57]=2)[CH:53]=[N:52]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 90030381HCID 90030381, 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 90030763HCID 90030763, compoundYield 23.6%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, 2-(4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(methylsulfonamido)phenyl)piperazin-1-yl)acetamide (80 mg, 0.1 mmol) was hydrolyzed with lithium hydroxide (13 mg, 0.3 mmol) in THF/methanol/Water (2/2/1 mL) to yield 15 mg (23.6% yield. 1H NMR (DMSO-d6, 400 MHz): δ 8.45-8.40 (m, 3H), 8.3 (s, 1H), 7.94 (s, 1H), 7.767-7.761 (d, 1H), 7.615-7.610 (d, 1H), 7.53-7.51 (d, 1H), 7.40-7.33 (m, 2H), 7.24-7.07 (m, 4H), 5.38 (s, 2H), 3.18 (s, 3H), 2.95-2.92 (m, 6H), 2.657 (s, 5H). MS: m/z=603.15 (M+1), HPLC: 93.36% in method A.

Workup

  1. customreaction conditions
  2. customto yield 15 mg (23.6% yield

Sources & evidence

ORD record
ord-4fc5869412714e45894718158310ed22
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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