Lithium Hydroxide → 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(4-(2-methoxyethyl)piperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 531795Notes

Reaction equation

HRID 531795 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[CH:66]=[N:67][C:68]([N:71]5[CH2:76][CH2:75][N:74]([CH2:77][CH2:78][O:79][CH3:80])[CH2:73][CH2:72]5)=[CH: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>[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[CH:66]=[N:67][C:68]([N:71]5[CH2:72][CH2:73][N:74]([CH2:77][CH2:78][O:79][CH3:80])[CH2:75][CH2:76]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 900312393-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(4-(2-methoxyethyl)piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 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 900648763-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(4-(2-methoxyethyl)piperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridineYield 37.7%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(4-(2-methoxyethyl)piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (70 mg, 0.105 mmol) was hydrolyzed by lithium hydroxide (25 mg, 0.63 mmol), THF/methanol/water (3/2/1 ml) to yield 20 mg (37.7% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.55-8.51 (m, 3H), 8.23 (s, 1H), 8.12-8.09 (dd, 1H), 7.97 (s, 1H), 7.73 (s, 1H), 7.40-7.30 (m, 1H), 7.15-7.10 (m, 2H), 7.06-7.00 (m, 2H), 5.45 (s, 2H), 3.79-3.76 (t, 2H), 3.60-2.90 (m, 8H). MS: m/z=512.15 (M+1), HPLC: 95.27% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-05b1daf9020c4d24bf5560e356ca42b1
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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