Lithium Hydroxide → HCID 90031360, compound

HRID 531808Notes

Reaction equation

HRID 531808 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:88]=[CH:89][CH:90]=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[CH2:76][CH2:75][CH:74]([OH:77])[CH2:73][CH2:72]5)=[N:69][CH:70]=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:88]=[CH:89][CH:90]=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[CH2:76][CH2:75][CH:74]([OH:77])[CH2:73][CH2:72]5)=[N:69][CH:70]=4)[CH:63]=3)[NH:58][CH:57]=2)[CH:53]=[N:52]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 118523927HCID 118523927, 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 90031360HCID 90031360, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, 1-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperidin-4-ol (160 mg, 0.25 mmol) was hydrolyzed with lithium hydroxide (33 mg, 0.77 mmol) in THF/methanol/water (3/3/1 mL) to yield 38 mg (25.4%) of desired product. 1H NMR (CD3OD, 300 MHz): δ 8.49-8.41 (m, 3H), 8.21 (s, 2H), 7.98 (s, 1H), 7.70 (s, 1H), 7.55-7.51 (s, 1H), 7.42-7.33 (m, 1H), 7.11-6.97 (m, 3H), 5.43 (s, 2H), 4.06-3.98 (m, 3H), 3.65-3.57 (m, 2H), 2.09-2.03 (m, 2H), 1.80-1.65 (m, 2H). MS: m/z=469.2 (M+1), HPLC: 93.72% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-0a4b36d4993a4505957f2f8995e01952
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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