Lithium Hydroxide → HCID 90064907, compound

HRID 531781Notes

Reaction equation

HRID 531781 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:93]=[CH:94][CH:95]=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]=[CH:67][C:68]([N:73]5[CH2:78][CH2:77][N:76]([CH2:79][C@@H:80]([OH:82])[CH3:81])[CH2:75][CH2:74]5)=[N:69][C:70]=4[O:71][CH3:72])[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:93]=[CH:94][CH:95]=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]=[CH:67][C:68]([N:73]5[CH2:74][CH2:75][N:76]([CH2:79][C@@H:80]([OH:82])[CH3:81])[CH2:77][CH2:78]5)=[N:69][C:70]=4[O:71][CH3:72])[CH:63]=3)[NH:58][CH:57]=2)[CH:53]=[N:52]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 90031140HCID 90031140, 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 90064907HCID 90064907, compoundYield 30.1%

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-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-6-methoxypyridin-2-yl) piperazin-1-yl)propan-2-ol (60 mg, 0.086 mmol) was hydrolyzed with lithium hydroxide (36 mg, 0.862 mmol) in THF/methanol/water (10/5/2 mL) to yield 14 mg (25% yield) of desired product. 1H NMR (CD3OD, 400 MHz): δ 8.615-8.612 (d, 1H), 8.51 (s, 1H), 8.20 (s, 1H), 7.95 (s, 1H), 7.82-7.80 (d, 1H), 7.76 (s, 1H), 7.41-7.36 (m, 1H), 7.14-7.12 (d, 1H), 7.08-7.01 (m, 2H), 6.61-6.59 (d, 1H), 5.44 (s, 2H), 4.52 (s, 2H), 4.29-4.24 (m, 1H), 3.96 (s, 3H), 3.74 (s, 2H), 3.36 (s, 2H), 3.26-3.11 (m, 4H), 1.28-1.27 (d, 2H). MS: m/z=542.2 (M+1), HPLC: 96.86% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-4b991c63c67c408aba59c8486ad8739e
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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