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Hydrochloric Acid → HCID 57377975, compound

HRID 527249
Notes
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Reaction equation

HRID 527249 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 25517Ammonium ChlorideHCID 16682925TrimethylaluminumHCID 67967926N-(2-((4-acetyloxazol-2-yl)methyl)-2H-1,2,3-triazol-4-yl)-2-methyl-5-(m-tolyl)oxazole-4-carboxamide

Product 1

HCID 57377975HCID 57377975, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8900HeptaneSolvent

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

  1. customThe layers were separated
  2. dry with materialphase was dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes