Lithium Hydroxide → HCID 90030966, compound

HRID 531707Notes

Reaction equation

HRID 531707 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:92]=[CH:93][CH:94]=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]([CH3:81])[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:92]=[CH:93][CH:94]=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[CH2:72][CH2:73][N:74]([CH2:77][C@@H:78]([OH:80])[CH3:79])[CH2:75][CH2:76]5)=[C:67]([CH3:81])[CH:66]=4)[CH:63]=3)[NH:58][CH:57]=2)[CH:53]=[N:52]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 90030672HCID 90030672, 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 90030966HCID 90030966, compoundYield 68%

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-methylphenyl)piperazin-1-yl)propan-2-ol (183 mg, 0.269 mmol) was hydrolyzed with lithium hydroxide (57 mg, 1.347 mmol) in THF/methanol/water (20/10/5 mL) to yield 96 mg (55.8% yield) of desired product. 1H NMR (CD3OD, 300 MHz): δ 8.63-8.62 (d, 1H), 8.54 (s, 1H), 8.26 (s, 1H), 7.97 (s, 1H), 7.77 (s, 1H), 7.65-7.63 (d, 1H), 7.60-7.56 (dd, 1H), 7.42-7.32 (q, 1H), 7.26-7.24 (d, 1H), 7.12-7.10 (d, 1H), 7.06-7.00 (m, 2H), 5.44 (s, 2H), 4.30-4.20 (m, 1H), 3.77-3.68 (t, 2H), 2.44 (s, 3H), 1.32-1.23 (m, 3H). MS: m/z=525.4 (M+1), HPLC: 90.77% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-157e42568333433bac2025b38564d46f
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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