Lithium Hydroxide → HCID 72944959, compound

HRID 531874Notes

Reaction equation

HRID 531874 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]([C:60]2[CH:61]=[C:62]3[C:68]([C:69]4[CH:70]=[N:71][N:72]([CH2:74][C:75]5[CH:80]=[CH:79][CH:78]=[C:77]([F:81])[CH:76]=5)[CH:73]=4)=[CH:67][N:66](S(C4C=CC(C)=CC=4)(=O)=O)[C:63]3=[N:64][CH:65]=2)[CH:50]=[N:51][C:52]=1[N:53]1[CH2:58][CH2:57][N:56]([CH3:59])[CH2:55][CH2:54]1.[OH-].[Li+]>C1COCC1.CO.O>[F:46][C:47]1[CH:48]=[C:49]([C:60]2[CH:61]=[C:62]3[C:68]([C:69]4[CH:70]=[N:71][N:72]([CH2:74][C:75]5[CH:80]=[CH:79][CH:78]=[C:77]([F:81])[CH:76]=5)[CH:73]=4)=[CH:67][NH:66][C:63]3=[N:64][CH:65]=2)[CH:50]=[N:51][C:52]=1[N:53]1[CH2:54][CH2:55][N:56]([CH3:59])[CH2:57][CH2:58]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 118524051HCID 118524051, 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 72944959HCID 72944959, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, 5-(5-fluoro-6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (150 mg, 0.234 mmol) was hydrolyzed with lithium hydroxide (98 mg, 2.34 mmol) in THF/methanol/water (12/4/4 mL) to yield 34 mg (30% yield) after purification by prep TLC using 8% methanol in chloroform as eluent. 1H NMR (CD3OD, 300 MHz): δ 8.459-8.452 (d, 1H), 8.36-8.34 (m, 2H), 8.24 (s, 1H), 7.94 (s, 1H), 7.85-7.79 (dd, 1H), 7.65 (s, 1H), 7.41-7.33 (q, 1H), 7.12-7.00 (m, 3H), 5.43 (s, 2H), 3.57-3.54 (t, 4H), 2.65-2.62 (m, 4H), 2.37 (s, 3H). MS: m/z=486.2 (M+1), HPLC: 98.03% in method A.

Workup

  1. customreaction conditions
  2. customto yield 34 mg (30% yield)
  3. customafter purification by prep TLC

Sources & evidence

ORD record
ord-e08aa7a4b7c4458fbbac4e2bf4210ead
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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