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Hydrochloric Acid → 2-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)-N,N-dimethylacetamide

HRID 17605
Notes
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Reaction equation

HRID 17605 reaction equation
C[Al](C)C.CCCCCC.Cl.[CH3:12][NH:13][CH3:14].[C:15]([C:17]1[C:22]2[N:23]=[C:24]([CH:26]3[CH2:28][CH2:27]3)[O:25][C:21]=2[C:20]([CH2:29][C:30]([O:32]C)=O)=[C:19]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:18]=1[CH3:40])#[N:16].Cl>C1(C)C=CC=CC=1>[C:15]([C:17]1[C:22]2[N:23]=[C:24]([CH:26]3[CH2:27][CH2:28]3)[O:25][C:21]=2[C:20]([CH2:29][C:30]([N:13]([CH3:14])[CH3:12])=[O:32])=[C:19]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:18]=1[CH3:40])#[N:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10473Dimethylamine, hydrochlorideHCID 86584505Trimethylaluminum hexaneHCID 86630881Methyl (4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)acetate

Product 1

HCID 685875632-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)-N,N-dimethylacetamideYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

At room temperature, trimethylaluminium/n-hexane solution (1.03 mol/l) (547 μl, 0.563 mmol) was added to a toluene (2 ml) suspension of dimethylamine hydrochloride (38.3 mg, 0.469 mmol), followed by stirring at room temperature for 30 minutes. Methyl (4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)acetate (I-295) (65.0 mg, 0.188 mmol) was added to the reaction liquid, followed by heating under reflux in an oil bath at 120° C. for 15 hours. With cooling with ice, 1 N hydrochloric acid was added to the reaction liquid. After extraction with ethyl acetate, the obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, then the insoluble matter was separated by filtration, and the residue obtained by concentration was purified by preparative TLC (eluent, chloroform:methanol=10:1, v/v) to obtain the entitled compound (56.0 mg, 83%) as a white solid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux in an oil bath at 120° C. for 15 hours
  3. additionwas added to the reaction liquid
  4. extractionAfter extraction with ethyl acetate
  5. washthe obtained organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe insoluble matter was separated by filtration
  8. customthe residue obtained by concentration
  9. customwas purified by preparative TLC (eluent, chloroform

Sources & evidence

ORD record
ord-c2b027ba9ea2410a96e4cf33a7a633b3
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737166B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes