Lithium Hydroxide → (S)-1-(4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)piperazin-1-yl)propan-2-ol

HRID 531697Notes

Reaction equation

HRID 531697 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:70]=[CH:69][C:68]([N:71]5[CH2:76][CH2:75][N:74]([CH2:77][C@@H:78]([OH:80])[CH3:79])[CH2:73][CH2:72]5)=[C:67]([O:81][CH3:82])[CH:66]=4)[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:70]=[CH:69][C:68]([N:71]5[CH2:76][CH2:75][N:74]([CH2:77][C@@H:78]([OH:80])[CH3:79])[CH2:73][CH2:72]5)=[C:67]([O:81][CH3:82])[CH:66]=4)[CH:63]=3)[NH:58][CH:57]=2)[CH:53]=[N:52]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 90030454(S)-1-(4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)piperazin-1-yl)propan-2-olHCID 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 72944535(S)-1-(4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)piperazin-1-yl)propan-2-olYield 65%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, (S)-1-(4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)piperazin-1-yl)propan-2-ol (70 mg, 0.100 mmol) was hydrolyzed with lithium hydroxide (13 mg, 0.302 mmol) in THF/methanol/water (2/2/1 mL) to yield 35 mg (65% yield). 1H NMR (CD3OD, 400 MHz): δ 8.48 (s, 1H), 8.34 (s, 1H), 8.20 (s, 1H), 7.95 (s, 1H), 7.39-7.36 (q, 1H), 7.30-7.28 (m, 2H), 7.13-7.11 (d, 2H), 7.07-7.02 (m, 2H), 5.45 (s, 2H), 4.20-4.30 (m, 1H), 3.99 (s, 3H), 3.60-3.80 (m, 4H), 3.1-3.3 (m, 3H), 1.29-1.28 (d, 3H). MS: m/z=541.6 (M+1), HPLC: 98.71% in method A.

Workup

  1. customreaction conditions
  2. customto yield 35 mg (65% yield)

Sources & evidence

ORD record
ord-60d63791a0884474866fdf9876663306
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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