Lithium Hydroxide → HCID 90031772, compound

HRID 531728Notes

Reaction equation

HRID 531728 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]([N:85]2[CH2:90][CH2:89][N:88]([CH2:91][C@@H:92]([OH:94])[CH3:93])[CH2:87][CH2:86]2)[CH:50]=[CH:51][C:52]=1[C:53]1[CH:54]=[C:55]2[C:61]([C:62]3[CH:63]=[N:64][N:65]([CH2:67][C:68]4[CH:73]=[CH:72][CH:71]=[C:70]([F:74])[CH:69]=4)[CH:66]=3)=[CH:60][N:59](S(C3C=CC(C)=CC=3)(=O)=O)[C:56]2=[N:57][CH:58]=1.[OH-].[Li+]>C1COCC1.CO.O>[F:46][C:47]1[CH:48]=[C:49]([N:85]2[CH2:90][CH2:89][N:88]([CH2:91][C@@H:92]([OH:94])[CH3:93])[CH2:87][CH2:86]2)[CH:50]=[CH:51][C:52]=1[C:53]1[CH:54]=[C:55]2[C:61]([C:62]3[CH:63]=[N:64][N:65]([CH2:67][C:68]4[CH:73]=[CH:72][CH:71]=[C:70]([F:74])[CH:69]=4)[CH:66]=3)=[CH:60][NH:59][C:56]2=[N:57][CH:58]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 118523908HCID 118523908, 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 90031772HCID 90031772, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, (S)-1-(4-(3-fluoro-4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazin-1-yl)propan-2-ol (100 mg, 0.146 mmol) was hydrolyzed with lithium hydroxide (30 mg, 0.73 mmol) in THF/methanol/water (3/2/1 mL) to yield 45 mg (58.4% yield) of desired product. 1H NMR (CD3OD, 300 MHz): δ 8.39-8.36 (m, 2H), 8.15 (s, 1H), 7.914-7.912 (d, 1H), 7.67 (s, 1H), 7.59-7.50 (t, 1H), 7.42-4.30 (m, 1H), 7.11-6.92 (m, 5H), 5.42 (s, 2H), 4.30-4.20 (m, 1H), 4.00-3.60 (m, 4H), 3.27-3.13 (m, 4H), 1.27-1.25 (d, 3H). MS: m/z=529.3 (M+1), HPLC: 95.98% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-aabf3b60b90e4d2b8ca83ee9050faed4
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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