Sodium Hydroxide → N-(2-(Methyloxy)-5-{4-[5-(tetrahydro-1,4-oxazepin-4(5H)-ylmethyl)-1,3,4-oxadiazol-2-yl]-1H-indazol-6-yl}-3-pyridinyl)methanesulfonamide

HRID 38887Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[CH:7][C:6]([C:14]2[CH:22]=[C:21]3[C:17]([CH:18]=[N:19][N:20]3S(C3C=CC=CC=3)(=O)=O)=[C:16]([C:32]3[O:33][C:34]([CH2:37][N:38]4[CH2:44][CH2:43][CH2:42][O:41][CH2:40][CH2:39]4)=[N:35][N:36]=3)[CH:15]=2)=[CH:5][N:4]=1.[OH-].[Na+]>O1CCOCC1>[CH3:1][O:2][C:3]1[C:8]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[CH:7][C:6]([C:14]2[CH:22]=[C:21]3[C:17]([CH:18]=[N:19][NH:20]3)=[C:16]([C:32]3[O:33][C:34]([CH2:37][N:38]4[CH2:44][CH2:43][CH2:42][O:41][CH2:40][CH2:39]4)=[N:35][N:36]=3)[CH:15]=2)=[CH:5][N:4]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of N-(2-(methyloxy)-5-{1-(phenylsulfonyl)-4-[5-(tetrahydro-1,4-oxazepin-4(5H)-ylmethyl)-1,3,4-oxadiazol-2-yl]-1H-indazol-6-yl}-3-pyridinyl)methanesulfonamide (50 mg, 0.078 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 2 h. The mixture was partitioned between ethyl acetate (5 ml) and saturated ammonium chloride solution (2 ml), separating the layers with a hydrophilic frit. The organic layer was evaporated to dryness under a stream of nitrogen to give the title compound as a pale brown solid (35 mg).

Workup

customThe mixture was partitioned between ethyl acetate (5 ml) and saturated ammonium chloride solution (2 ml)
customseparating the layers with a hydrophilic frit
customThe organic layer was evaporated to dryness under a stream of nitrogen

Sources & evidence

ORD record: ord-714d57e088dc4977a6172e5559100308
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524751B2

Reaction notes

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