Hydrochloric Acid → HCID 57377975, compound

HRID 527249Notes

Reaction equation

N#N.[C:3]([C:6]1[N:7]=[C:8]([CH2:11][N:12]2[N:16]=[C:15]([NH:17][C:18]([C:20]3[N:21]=[C:22]([CH3:32])[O:23][C:24]=3[C:25]3[CH:26]=[C:27]([CH3:31])[CH:28]=[CH:29][CH:30]=3)=[O:19])[CH:14]=[N:13]2)[O:9][CH:10]=1)(=[O:5])[CH3:4].[CH3:33][Al](C)C.[Cl-].[NH4+].Cl>C(Cl)Cl.CCCCCCC>[OH:5][C:3]([C:6]1[N:7]=[C:8]([CH2:11][N:12]2[N:16]=[C:15]([NH:17][C:18]([C:20]3[N:21]=[C:22]([CH3:32])[O:23][C:24]=3[C:25]3[CH:26]=[C:27]([CH3:31])[CH:28]=[CH:29][CH:30]=3)=[O:19])[CH:14]=[N:13]2)[O:9][CH:10]=1)([CH3:33])[CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of N-(2-((4-acetyloxazol-2-yl)methyl)-2H-1,2,3-triazol-4-yl)-2-methyl-5-(m-tolyl)oxazole-4-carboxamide (622 mg, 1.53 mmol) in CH2Cl2 (15 mL) was treated at 0° C. with AlMe3 (2.3 mL of a 2.0M solution in heptane, 4.6 mmol) and the resulting mixture was stirred for 2 h at 0° C. The reaction mixture was carefully poured into a sat. aq. solution of ammonium chloride (10 mL) and diluted with CH2Cl2 (20 mL). 1N HCl (10 mL) was then added. The layers were separated and the org. phase was dried over Na2SO4, filtered and the solvents were removed under reduced pressure. Purification of the residue by FC (3:7 hept-EA) gave the title compound as a white solid: TLC: rf (3:7 hept-EA)=0.28. LC-MS-conditions 06: tR=0.85 min, [M+H]+=423.17.

Workup

customThe layers were separated
dry with materialphase was dried over Na2SO4
filtrationfiltered
customthe solvents were removed under reduced pressure
customPurification of the residue by FC (3:7 hept-EA)

Sources & evidence

ORD record: ord-a3c38e95410340279dc2bc41cf2c8517
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346793B2

Reaction notes

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