Lithium Hydroxide → 2-(4-(3-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)benzyl) piperidin-1-yl) acetamide

HRID 531885Notes

Reaction equation

HRID 531885 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:92]=[CH:93][CH:94]=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]=[C:67]([CH:79]=[CH:80][CH:81]=4)[CH2:68][CH:69]4[CH2:74][CH2:73][N:72]([CH2:75][C:76]([NH2:78])=[O:77])[CH2:71][CH2:70]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:92]=[CH:93][CH:94]=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]=[C:67]([CH:79]=[CH:80][CH:81]=4)[CH2:68][CH:69]4[CH2:74][CH2:73][N:72]([CH2:75][C:76]([NH2:78])=[O:77])[CH2:71][CH2:70]4)[CH:63]=3)[NH:58][CH:57]=2)[CH:53]=[N:52]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 900304052-(4-(3-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)benzyl)piperidin-1-yl) acetamideHCID 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 729449582-(4-(3-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)benzyl) piperidin-1-yl) acetamideYield 43.5%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, 2-(4-(3-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)benzyl)piperidin-1-yl) acetamide (30 mg, 0.044 mmol) was hydrolyzed by lithium hydroxide (18 mg, 0.44 mmol) in THF/methanol/water (2/2/1 ml) to yield 10 mg (43.4% yield) of the titled compound. 1H NMR (DMSO-d6, 400 MHz): δ 8.516-8.512 (d, 1H), 8.43 (s, 1H), 8.347-8.343 (d, 1H), 7.98 (s, 1H), 7.77 (s, 1H), 7.59-7.54 (m, 2H), 7.42-7.38 (t, 2H), 7.17-7.09 (m, 5H), 5.41 (s, 2H), 2.78 (s, 4H), 2.65-2.55 (m, 2H), 1.99-1.93 (t, 2H), 1.59-1.56 (m, 3H), 1.31-1.23 (m, 3H). MS: m/z=523.4 (M+1), HPLC: 91.01% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-27b9d593f7144f7fbdd0b797a72c25ac
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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