Lithium Hydroxide → HCID 72944957, compound

HRID 531890Notes

Reaction equation

HRID 531890 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[C:55]([CH3:56])=[C:54]([C:57]2[C:65]3[C:60](=[N:61][CH:62]=[C:63]([C:66]4[CH:67]=[C:68]([N:72]5[CH2:77][CH2:76][N:75]([CH2:78][CH2:79][OH:80])[CH2:74][CH2:73]5)[CH:69]=[CH:70][CH:71]=4)[CH:64]=3)[N:59](S(C3C=CC(C)=CC=3)(=O)=O)[CH:58]=2)[C:53]([CH3:91])=[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[C:55]([CH3:56])=[C:54]([C:57]2[C:65]3[C:60](=[N:61][CH:62]=[C:63]([C:66]4[CH:67]=[C:68]([N:72]5[CH2:77][CH2:76][N:75]([CH2:78][CH2:79][OH:80])[CH2:74][CH2:73]5)[CH:69]=[CH:70][CH:71]=4)[CH:64]=3)[NH:59][CH:58]=2)[C:53]([CH3:91])=[N:52]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 90031775HCID 90031775, 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 72944957HCID 72944957, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using the same reaction conditions as described in step-iii of example-1, 2-(4-(3-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) piperazin-1-yl)ethanol (58 mg, 0.085 mmol) was hydrolyzed by lithium hydroxide (36 mg, 0.85 mmol), THF/Methanol/water (12/6/3 ml) to yield 7 mg (16%) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 8.46-8.45 (d, 1H), 7.87-7.86 (d, 1H), 7.39-7.31 (m, 3H), 7.16 (s, 1H), 7.10-7.08 (m, 1H), 7.04-6.97 (m, 3H), 6.87-6.84 (m, 1H), 3.75-3.74 (t, 2H), 2.82 (b, 4H), 2.53 (m, 2H), 2.21 (s, 3H), 2.17 (s, 3H). MS: m/z=525.0 (M+1), HPLC: 91.007% in method A.

Workup

  1. customthe same reaction conditions

Sources & evidence

ORD record
ord-8cfe19efee72444fb2e20ad453d0f277
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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