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

HRID 531773Notes

Reaction equation

HRID 531773 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.[CH3:46][N:47]1[CH2:52][CH2:51][N:50]([C:53]2[N:58]=[CH:57][C:56]([C:59]3[CH:60]=[C:61]4[C:67]([C:68]5[CH:69]=[N:70][N:71]([CH2:73][CH2:74][C:75]6[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=6)[CH:72]=5)=[CH:66][N:65](S(C5C=CC(C)=CC=5)(=O)=O)[C:62]4=[N:63][CH:64]=3)=[CH:55][CH:54]=2)[CH2:49][CH2:48]1.[OH-].[Li+]>C1COCC1.CO.O>[CH3:46][N:47]1[CH2:48][CH2:49][N:50]([C:53]2[N:58]=[CH:57][C:56]([C:59]3[CH:60]=[C:61]4[C:67]([C:68]5[CH:69]=[N:70][N:71]([CH2:73][CH2:74][C:75]6[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=6)[CH:72]=5)=[CH:66][NH:65][C:62]4=[N:63][CH:64]=3)=[CH:55][CH:54]=2)[CH2:51][CH2:52]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 900315215-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(1-phenethyl-1H-pyrazol-4-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 729446485-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridineYield 98.5%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, 5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(1-phenethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (50 mg, 0.088 mmol) was hydrolyzed with lithium hydroxide (18 mg, 0.44 mmol) in THF/methanol/water (2/2/1 mL) to yield 40 mg (98.5% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.55-8.50 (d, 2H), 8.40 (s, 1H), 8.19-8.10 (dd, 1H), 7.89-7.84 (d, 2H), 7.68 (s, 1H), 7.24-7.21 (m, 3H), 7.15-7.11 (m, 3H), 4.50-4.50 (t, 2H), 3.20-3.10 (t, 2H), 2.98 (s, 3H). MS: m/z=464.2 (M+1), HPLC: 93.96% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-e952aabfe2e1491fa77dabd8a917a5d8
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

Loading…