Lithium Hydroxide → HCID 72944748, compound

HRID 531471Notes

Reaction equation

HRID 531471 reaction equation
[CH3:1][O:2][C:3]1[CH:44]=[CH:43][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[C:21]4[C:16](=[N:17][CH:18]=[C:19]([C:22]5[CH:23]=[C:24]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:25]=[CH:26][CH:27]=5)[CH:20]=4)[N:15](S(C4C=CC(C)=CC=4)(=O)=O)[CH:14]=3)[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[OH-].[Li+]>C1COCC1.O.CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[C:21]4[C:16](=[N:17][CH:18]=[C:19]([C:22]5[CH:23]=[C:24]([NH:28][S:29]([CH3:32])(=[O:30])=[O:31])[CH:25]=[CH:26][CH:27]=5)[CH:20]=4)[NH:15][CH:14]=3)[CH:10]=[N:9]2)=[CH:43][CH:44]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 118523966N-(3-(3-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide

Product 1

HCID 72944748HCID 72944748, compoundYield 9.57%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, N-(3-(3-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methane sulfon amide (250 mg, 0.39 mmol) was hydrolyzed with lithium hydroxide (66 mg, 1.6 mmol) in THF/water/methanol (4/3/1 ml) mixture to afford 15 mg (9.57% yield) of the pure product after purification by prep TLC using 2% methanol in DCM as eluent. 1H NMR (DMSO-d6, 300 MHz): δ 11.79 (s, 1H), 9.83 (s, 1H), 8.469 (s, 1H), 8.33-8.31 (d, 2H), 7.91 (s, 1H), 7.75 (s, 1H), 7.52-7.43 (m, 3H), 7.27-7.22 (t, 3H), 6.91-6.89 (d, 2H), 5.28 (s, 2H), 3.72 (s, 3H), 3.05 (s, 3H). MS: m/z=474.2 (M+1), HPLC: 94.18% in Method-C.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-99918f27392a48598220737cd972eefb
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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