Sodium Hydroxide → N-[5-[4-(5-{[(2R,6S)-2,6-Dimethyl-4-morpholinyl]methyl}-1,3,4-oxadiazol-2-yl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]methanesulfonamide

HRID 38867Notes

Reaction equation

[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([CH2:9][C:10]2[O:14][C:13]([C:15]3[CH:23]=[C:22]([C:24]4[CH:25]=[C:26]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[C:27]([O:30][CH3:31])=[N:28][CH:29]=4)[CH:21]=[C:20]4[C:16]=3[CH:17]=[N:18][N:19]4S(C3C=CC=CC=3)(=O)=O)=[N:12][N:11]=2)[CH2:3]1.[OH-].[Na+]>O1CCOCC1>[CH3:8][C@H:6]1[O:7][C@@H:2]([CH3:1])[CH2:3][N:4]([CH2:9][C:10]2[O:14][C:13]([C:15]3[CH:23]=[C:22]([C:24]4[CH:25]=[C:26]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[C:27]([O:30][CH3:31])=[N:28][CH:29]=4)[CH:21]=[C:20]4[C:16]=3[CH:17]=[N:18][NH:19]4)=[N:12][N:11]=2)[CH2:5]1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of N-[5-[4-(5-{[(2R,6S)-2,6-dimethyl-4-morpholinyl]methyl}-1,3,4-oxadiazol-2-yl)-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]methanesulfonamide (106 mg, 0.162 mmol) in 1,4-dioxane (1 ml) was added 2M sodium hydroxide (1 ml, 2.000 mmol) and the mixture stirred at 20° C. for 18 h. The mixture was evaporated in vacuo and the residue partitioned between ethyl acetate (10 ml) and saturated ammonium chloride (5 ml), separated by hydrophilic frit and purified by silica (5 g) cartridge using a gradient of dichloromethane and methanol to give a pale brown solid 50 mg which was purified by MDAP to give the title compound as a white solid (32 mg).

Workup

customThe mixture was evaporated in vacuo
customthe residue partitioned between ethyl acetate (10 ml) and saturated ammonium chloride (5 ml)
customseparated by hydrophilic frit
custompurified by silica (5 g) cartridge

Sources & evidence

ORD record: ord-9cbd8803efe94c0483af62b65f7c83a9
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524751B2

Reaction notes

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