Sodium Hydroxide → HCID 178521965, compound

HRID 82712Notes

Reaction equation

HRID 82712 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2C(=O)[O:11][N:10]=[C:9]2[C:14]2[C:15]([NH:19][C:20]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:21])=[N:16][O:17][N:18]=2)[CH:5]=[CH:6][CH:7]=1.[OH-:29].[Na+]>C(O)C.O>[NH:8]([C:9]([N:19]([C:20]([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:21])[C:15]1[C:14]([C:9](=[N:10][OH:11])[NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)=[N:18][O:17][N:16]=1)=[O:29])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=1.[NH:22]([C:20]([NH:19][C:15]1[C:14]([C:9](=[N:10][OH:11])[NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)=[N:18][O:17][N:16]=1)=[O:21])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 58755042HCID 58755042, compound

Product 2

HCID 178521965HCID 178521965, compoundYield 38%HCID 178521967HCID 178521967, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of N-{4-[4-(3-chlorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl}-N′-phenylurea (17 mg, 43 μmol) in ethanol (1.5 mL) was treated with 2.0 M sodium hydroxide in water (0.3 mL) and stirred for 30 min. Purification of the crude reaction mixture by preparative HPLC gave the desired product 4-[(anilinocarbonyl)amino]-N-(3-chlorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide (6 mg, 38%). LCMS for C16H14ClN6O3 (M+H)+: m/z=373.0.

Workup

  1. customPurification of the crude
  2. customreaction mixture by preparative HPLC

Sources & evidence

ORD record
ord-5161f3b886eb4559b35bf9d4b9e3048a
Source dataset
uspto-grants-2014_09
Patent number
US08846726B2

Reaction notes

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