Lithium Hydroxide → 5-(3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy-N-methylbenzenesulfonamide

HRID 531506Notes

Reaction equation

HRID 531506 reaction equation
[F:1]C1C=CC=CC=1CN1C=C(C2C3C(=NC=C(C4C=C(NS(C)(=O)=O)C=CC=4)C=3)NC=2)C=N1.F[C:35]1[CH:80]=[CH:79][C:78]([F:81])=[CH:77][C:36]=1[CH2:37][N:38]1[C:42]([CH3:43])=[C:41]([C:44]2[C:52]3[C:47](=[N:48][CH:49]=[C:50]([C:53]4[CH:54]=[CH:55][C:56]([O:64][CH3:65])=[C:57]([S:59]([NH:62][CH3:63])(=[O:61])=[O:60])[CH:58]=4)[CH:51]=3)[N:46](S(C3C=CC(C)=CC=3)(=O)=O)[CH:45]=2)[C:40]([CH3:76])=[N:39]1.[OH-].[Li+]>C1COCC1.CO.O>[F:81][C:78]1[CH:77]=[C:36]([CH:35]=[C:80]([F:1])[CH:79]=1)[CH2:37][N:38]1[C:42]([CH3:43])=[C:41]([C:44]2[C:52]3[C:47](=[N:48][CH:49]=[C:50]([C:53]4[CH:54]=[CH:55][C:56]([O:64][CH3:65])=[C:57]([S:59]([NH:62][CH3:63])(=[O:60])=[O:61])[CH:58]=4)[CH:51]=3)[NH:46][CH:45]=2)[C:40]([CH3:76])=[N:39]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 72944747N-(3-(3-(1-(2-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methanesulfonamideHCID 1185239145-(3-(1-(2,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy-N-methylbenzenesulfonamide

Product 1

HCID 900310245-(3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy-N-methylbenzenesulfonamideYield 11.4%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example 1, 5-(3-(1-(2,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy-N-methylbenzenesulfonamide (180 mg, 0.2604 mmol) was hydrolyzed by lithium hydroxide (109 mg, 2.604 mmol), THF/Methanol/water (24/12/6 ml) to yield 16 mg (11.4% yield) of the titled compound after purification by preparative TLC (SiO2-1000 micron eluted by 3% MeOH in CHCl3). 1H NMR (CD3OD, 300 MHz): δ 8.382 (m, 1H), 7.940-7.935 (d, 1H), 7.816-7.779 (m, 2H), 7.342 (s, 1H), 7.241-7.213 (d, 1H), 6.68-6.64 (m, 1H), 5.275 (s, 2H), 3.914 (s, 3H), 2.441 (s, 3H), 2.128-2.101 (d, 6H). MS: m/z=538.1 (M+1); HPLC: 95.69% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-a3457fcfb86a4fd6ad78361b3848212a
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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