Lithium Hydroxide → N-(5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)ethanesulfonamide

HRID 531495Notes

Reaction equation

HRID 531495 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:46]=[CH:47][CH:48]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[C:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[CH:23][C:24]([O:33][CH3:34])=[C:25]([NH:27][S:28]([CH2:31][CH3:32])(=[O:30])=[O:29])[CH:26]=4)[CH:19]=3)[N:14](S(C3C=CC(C)=CC=3)(=O)=O)[CH:13]=2)[C:8]([CH3:45])=[N:7]1.[OH-].[Li+]>C1COCC1.CO.O>[F:1][C:2]1[CH:3]=[C:4]([CH:46]=[CH:47][CH:48]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[C:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[CH:23][C:24]([O:33][CH3:34])=[C:25]([NH:27][S:28]([CH2:31][CH3:32])(=[O:30])=[O:29])[CH:26]=4)[CH:19]=3)[NH:14][CH:13]=2)[C:8]([CH3:45])=[N:7]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90030730N-(5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy phenyl)ethane sulfonamide

Product 1

HCID 72944951N-(5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)ethanesulfonamideYield 16.5%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, N-(5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy phenyl)ethane sulfonamide (200 mg, 0.291 mmol) was hydrolyzed by lithium hydroxide (36 mg, 0.87 mmol) in THF/Methanol/Water (10/3/2 ml) to give 25 mg (16.5% yield) after purification by flash chromatography. 1H NMR (DMSO-d6, 300 MHz): δ 11.9 (s, 1H), 9.02 (s, 1H), 8.45 (s, 1H), 7.79 (s, 1H), 7.54-7.49 (m, 3H), 7.19-7.0 (m, 4H), 5.33 (s, 2H), 3.86 (s, 3H), 3.06-3.04 (m, 2H0, 2.17-2.13 (d, 6H), 1.27-1.23 (t, 3H). MS: m/z=534.8 (M+1), HPLC: 90.27% (Method-B).

Workup

  1. customreaction conditions
  2. customto give 25 mg (16.5% yield)
  3. customafter purification by flash chromatography

Sources & evidence

ORD record
ord-344fea4eb5694e12bfd01d70b2565ff8
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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