Ammonia → tert-butyl 2-(N-(4-(5-amino-1,2,4-oxadiazol-3-yl)benzyl)-4-nitrobenzamido)acetate

HRID 923612Notes

Reaction equation

[OH:1][NH:2][C:3]([C:5]1[CH:31]=[CH:30][C:8]([CH2:9][N:10]([CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:11](=[O:21])[C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)=[NH:4].Cl[C:33](Cl)(Cl)C(OC(=O)C(Cl)(Cl)Cl)=O.[NH3:45]>O1CCOCC1.CO>[NH2:45][C:33]1[O:1][N:2]=[C:3]([C:5]2[CH:6]=[CH:7][C:8]([CH2:9][N:10]([CH2:22][C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[C:11](=[O:21])[C:12]3[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=3)=[CH:30][CH:31]=2)[N:4]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Prepared from INT-57. To a stirring suspension of tert-butyl 2-(N-(4-(N-hydroxycarbamimidoyl)benzyl)-4-nitrobenzamido)acetate INT-57 (820 mg, 1.91 mmol) in dioxane (10 mL) was added 2,2,2-trichloroacetic anhydride (420 μL, 2.30 mmol) and heated to 120° C. for 2 h. To this mixture was added 7 M ammonia in MeOH (10 mL) and stirred at room temperature for 18 h. The reaction mixture was pre-absorbed onto silica gel and purified by chromatography (EA/hexanes) to afford 342 mg (39%) of tert-butyl 2-(N-(4-(5-amino-1,2,4-oxadiazol-3-yl)benzyl)-4-nitrobenzamido)acetate) INT-67 as a white solid. LCMS-ESI (m/z) calculated for C22H23N5O6: 453; found 454 [M+H]+, tR=2.30 min (Method 10).

Workup

customPrepared from INT-57
customThe reaction mixture was pre-absorbed onto silica gel
custompurified by chromatography (EA/hexanes)

Sources & evidence

ORD record: ord-c6945220c3ba4fc7a807a9aeb91294a1
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278910B2

Reaction notes

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