Lithium Hydroxide → HCID 90031030, compound

HRID 531793Notes

Reaction equation

HRID 531793 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.[CH2:46]([N:53]1[CH:57]=[C:56]([C:58]2[C:66]3[C:61](=[N:62][CH:63]=[C:64]([C:67]4[CH:68]=[CH:69][C:70]([N:73]5[CH2:78][CH2:77][N:76]([CH2:79][C@@H:80]([OH:82])[CH3:81])[CH2:75][CH2:74]5)=[N:71][CH:72]=4)[CH:65]=3)[N:60](S(C3C=CC(C)=CC=3)(=O)=O)[CH:59]=2)[CH:55]=[N:54]1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.[OH-].[Li+]>C1COCC1.CO.O>[CH2:46]([N:53]1[CH:57]=[C:56]([C:58]2[C:66]3[C:61](=[N:62][CH:63]=[C:64]([C:67]4[CH:68]=[CH:69][C:70]([N:73]5[CH2:74][CH2:75][N:76]([CH2:79][C@@H:80]([OH:82])[CH3:81])[CH2:77][CH2:78]5)=[N:71][CH:72]=4)[CH:65]=3)[NH:60][CH:59]=2)[CH:55]=[N:54]1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 118524059HCID 118524059, 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 90031030HCID 90031030, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, (S)-1-(4-(5-(3-(1-benzyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)propan-2-ol (155 mg, 0.239 mmol) was hydrolyzed with lithium hydroxide (50 mg, 1.19 mmol) in THF/methanol/water (4/4/2 mL) to yield 40 mg (24.9% yield) of desired product. 1H NMR (DMSO-d6, 300 MHz): δ 11.8 (s, 1H), 9.6 (s, 1H), 8.63-8.62 (d, 1H), 8.52-8.51 (d, 1H), 8.42 (s, 1H), 8.36-8.35 (d, 1H), 8.11-8.07 (dd, 1H), 7.97 (s, 1H), 7.769-7.761 (d, 1H), 7.38-7.27 (m, 4H), 7.10-7.07 (d, 1H), 5.38 (s, 2H), 4.47-4.35 (m, 2H), 4.20-4.10 (m, 1H), 3.50-3.00 (m, 6H), 1.15-1.13 (d, 3H). MS: m/z=494.6 (M+1), HPLC: 96.64% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-31a2ab08b95b4614889f21448acd14b1
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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