Lithium Hydroxide → HCID 90030331, compound

HRID 531688Notes

Reaction equation

HRID 531688 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[CH: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[CH:54]=[CH:55][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:57][CH:58]=2)[CH2:51][CH2:52]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 118523923HCID 118523923, 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 90030331HCID 90030331, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, 5-(4-(4-methylpiperazin-1-yl)phenyl)-3-(1-phenethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (60 mg, 0.097 mmol) was hydrolyzed by lithium hydroxide (12 mg, 0.291 mmol) in THF/methanol/water (1/1/1 ml) to afford 20 mg (45.0% yield) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 8.24 (s, 1H), 7.88 (s, 1H), 7.78 (s, 1H), 7.67-7.65 (d, 2H), 7.61 (s, 1H), 7.28-7.15 (m, 6H), 4.49-4.45 (t, 2H), 4.00-3.97 (d, 2H), 3.69-3.66 (d, 2H), 3.23-3.12 (m, 6H), 3.02 (s, 3H). MS: m/z=462.9 (M+1), HPLC: 96.28% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-11fdadcea10546cf82844906085eb0d0
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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