Lithium Hydroxide → HCID 72944536, compound

HRID 531710Notes

Reaction equation

HRID 531710 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:93]=[CH:94][CH:95]=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)=[CH:67][C:66]=4[O:81][CH3:82])[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:93]=[CH:94][CH:95]=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)=[CH:67][C:66]=4[O:81][CH3:82])[CH:63]=3)[NH:58][CH:57]=2)[CH:53]=[N:52]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 90031033HCID 90031033, 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 72944536HCID 72944536, compoundYield 29%

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)-3-methoxyphenyl)piperazin-1-yl)propan-2-ol (120 mg, 0.172 mmol) was hydrolyzed with lithium hydroxide (22 mg, 0.518 mmol) in THF/methanol/water (2/2/1 mL) to yield 27 mg (29.0% yield). 1H NMR (CD3OD, 400 MHz): δ 8.55-8.54 (d, 1H), 8.438-8.434 (d, 1H), 8.19 (s, 1H), 7.94 (s, 1H), 7.76 (s, 1H), 7.42-7.38 (m, 2H), 7.14-7.12 (d, 1H), 7.05-7.03 (qd, 2H), 6.80-6.76 (m, 2H), 5.44 (s, 2H), 4.29-4.24 (m, 1H), 3.99-3.96 (m, 2H), 3.86 (s, 3H), 3.75-3.38 (m, 2H), 3.29-3.12 (m, 6H), 1.29-1.28 (d, 3H). MS: m/z=541.4 (M+1), HPLC: 92.28% in method A.

Workup

  1. customreaction conditions
  2. customto yield 27 mg (29.0% yield)

Sources & evidence

ORD record
ord-ca9e6be6da234f198cb3f9f5c603dfc6
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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