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

HRID 531777Notes

Reaction equation

HRID 531777 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:54]1[CH:58]=[C:57]([C:59]2[C:67]3[C:62](=[N:63][CH:64]=[C:65]([C:68]4[CH:69]=[CH:70][C:71]([N:74]5[CH2:79][CH2:78][N:77]([CH2:80][C@@H:81]([OH:83])[CH3:82])[CH2:76][CH2:75]5)=[N:72][CH:73]=4)[CH:66]=3)[N:61](S(C3C=CC(C)=CC=3)(=O)=O)[CH:60]=2)[CH:56]=[N:55]1)[CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.[OH-].[Li+]>C1COCC1.CO.O>[CH2:46]([N:54]1[CH:58]=[C:57]([C:59]2[C:67]3[C:62](=[N:63][CH:64]=[C:65]([C:68]4[CH:69]=[CH:70][C:71]([N:74]5[CH2:79][CH2:78][N:77]([CH2:80][C@@H:81]([OH:83])[CH3:82])[CH2:76][CH2:75]5)=[N:72][CH:73]=4)[CH:66]=3)[NH:61][CH:60]=2)[CH:56]=[N:55]1)[CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 118524061(S)-1-(4-(5-(3-(1-phenethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)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 90030958(S)-1-(4-(5-(3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl) piperazin-1-yl)propan-2-olYield 83.3%

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-phenethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)propan-2-ol (80 mg, 0.12 mmol) was hydrolyzed with lithium hydroxide (25 mg, 0.6 mmol) in THF/methanol/water (2/2/1 mL) to yield 50 mg (83.3% yield) of desired product. 1H NMR (CD3OD, 300 MHz): δ 8.53-8.52 (d, 2H), 8.36-8.35 (d, 1H), 8.12-8.08 (dd, 1H), 7.896-7.893 (d, 1H), 7.818-7.816 (d, 1H), 7.67 (s, 1H), 7.26-7.20 (m, 3H), 7.17-7.12 (m, 3H), 4.47-4.43 (d, 2H), 4.30-4.20 (t, 1H), 3.60-3.40 (bs, 4H), 3.25-3.10 (m, 4H), 1.27-1.25 (d, 3H). MS: m/z=408.6 (M+1), HPLC: 93.50% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-29be7f2ec00645e886b0e648f47b13a3
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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