Lithium Hydroxide → HCID 90064855, compound

HRID 531831Notes

Reaction equation

HRID 531831 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[CH2:77][CH2:76][CH2:75][N:74]([CH2:78][C@@H:79]([OH:81])[CH3:80])[CH2:73][CH2:72]5)=[CH:67][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:66]=[CH:67][C:68]([N:71]5[CH2:77][CH2:76][CH2:75][N:74]([CH2:78][C@@H:79]([OH:81])[CH3:80])[CH2:73][CH2:72]5)=[CH:69][CH:70]=4)[CH:63]=3)[NH:58][CH:57]=2)[CH:53]=[N:52]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 118524062HCID 118524062, 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 90064855HCID 90064855, compoundYield 42.8%

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)phenyl)-1,4-diazepan-1-yl) propan-2-ol (100 mg, 0.147 mmol) was hydrolyzed with lithium hydroxide (31 mg, 0.736 mmol) in THF/methanol/water (2/2/1 mL) to yield 33 mg (42.8% yield) of desired product. 1H NMR (CDCl3, 300 MHz): δ 8.83 (s, 1H), 8.538-8.531 (d, 1H), 8.13-8.12 (d, 1H), 7.86 (s, 1H), 7.70 (s, 1H), 7.52-7.49 (d, 2H), 7.39-7.30 (m, 2H), 7.07-6.91 (m, 3H), 6.82-6.79 (d, 2H), 5.38 (s, 2H), 3.85-3.75 (m, 1H), 3.70-3.55 (m, 4H), 3.15-3.00 (m, 1H), 2.90-2.80 (m, 2H), 2.70-2.55 (m, 2H), 2.35-2.25 (m, 1H), 2.15-1.95 (m, 2H), 1.14-1.12 (d, 3H). MS: m/z=525.3 (M+1), HPLC: 92.75% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-2acd2224aeb74165aeaa5d7b7eb45352
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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