Sodium periodate → 1-oxo-thiomorpholine-4-carboxylic acid (4-{[2-(2-methyl-2H-indazol-6-ylcarbamoyl)-phenylamino]-methyl}-pyridin-2-yl)-amide

HRID 2100412Notes

Reaction equation

HRID 2100412 reaction equation
[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[C:6]([NH:11][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[NH:20][CH2:21][C:22]3[CH:27]=[CH:26][N:25]=[C:24]([NH:28][C:29]([N:31]4[CH2:36][CH2:35][S:34][CH2:33][CH2:32]4)=[O:30])[CH:23]=3)=[O:13])[CH:7]=[CH:8]2)=[N:3]1.I([O-])(=O)(=O)=[O:38].[Na+]>CO.O>[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[C:6]([NH:11][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[NH:20][CH2:21][C:22]3[CH:27]=[CH:26][N:25]=[C:24]([NH:28][C:29]([N:31]4[CH2:32][CH2:33][S:34](=[O:38])[CH2:35][CH2:36]4)=[O:30])[CH:23]=3)=[O:13])[CH:7]=[CH:8]2)=[N:3]1

Participants

4

Reactant 2

HCID 23667635Sodium periodateHCID 57798922thiomorpholine-4-carboxylic acid (4-{[2-(2-methyl-2H-indazol-6-ylcarbamoyl)-phenylamino]-methyl}-pyridin-2-yl)-amide

Product 1

HCID 116060301-oxo-thiomorpholine-4-carboxylic acid (4-{[2-(2-methyl-2H-indazol-6-ylcarbamoyl)-phenylamino]-methyl}-pyridin-2-yl)-amideYield 58%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of thiomorpholine-4-carboxylic acid (4-{[2-(2-methyl-2H-indazol-6-ylcarbamoyl)-phenylamino]-methyl}-pyridin-2-yl)-amide (50 mg, 0.1 mmol) and sodium periodate (43 mg, 0.2 mmol) in MeOH/water (3:1, 4 mL) was stirred overnight at rt. The reaction was partitioned between EtOAc and brine and the organic phase dried, filtered and concentrated in vacuo to give 1-oxo-thiomorpholine-4-carboxylic acid (4-{[2-(2-methyl-2H-indazol-6-ylcarbamoyl)-phenylamino]-methyl}-pyridin-2-yl)-amide (30 mg, 58%) as a solid; 1H-NMR (300 MHz, d6-DMSO) 10.14 (1H, s), 9.37 (1H, s), 8.25 (1H, s), 8.17 (1H, d), 8.10 (1H, s), 7.96 (1H, t), 7.82 (1H, s), 7.71-7.74 (1H, m), 7.63 (1H, d), 7.23-7.32 (2H, m), 6.96-6.98 (1H, m), 6.67 (1H, t), 6.54 (1H, d), 4.45 (2H, d), 4.13 (3H, s), 3.99-4.04 (2H, m), 3.66-3.74 (2H, m), 2.84-2.93 (2H, m), 2.65-2.70 (2H, m); m/z (LC-ES+) 518 [M+H]+.

Workup

  1. customThe reaction was partitioned between EtOAc and brine
  2. customthe organic phase dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ca768bdc4ea041518d7ddfad9691ca02
Source dataset
uspto-grants-2009_08
Patent number
US07572794B2

Reaction notes

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