Aluminum(III) Chloride → 2-tert-Butyl-7-[(S)-3-(dimethylamino)pyrrolidin-1-yl]-6-(3-hydroxyphenyl)-5-methyl-1,3-benzoxazole-4-carbonitrile

HRID 17283

Reaction equation

HRID 17283 reaction equation
[C:1]([C:5]1[O:6][C:7]2[C:8](=[C:10]([C:31]#[N:32])[C:11]([CH3:30])=[C:12]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28]C)[CH:23]=3)[C:13]=2[N:14]2[CH2:18][CH2:17][C@H:16]([N:19]([CH3:21])[CH3:20])[CH2:15]2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].O.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[C:1]([C:5]1[O:6][C:7]2[C:8](=[C:10]([C:31]#[N:32])[C:11]([CH3:30])=[C:12]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[CH:23]=3)[C:13]=2[N:14]2[CH2:18][CH2:17][C@H:16]([N:19]([CH3:20])[CH3:21])[CH2:15]2)[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6451240Aluminum(III) Chloride2×HCID 685853342-tert-butyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-(3-methoxyphenyl)-5-methyl-1,3-benzoxazole-4-carbonitrileHCID 86585896Sodium bicarbonate water

Product 1

HCID 685848602-tert-Butyl-7-[(S)-3-(dimethylamino)pyrrolidin-1-yl]-6-(3-hydroxyphenyl)-5-methyl-1,3-benzoxazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

2-tert-Butyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-(3-methoxyphenyl)-5-methyl-1,3-benzoxazole-4-carbonitrile (I-23) (10 mg, 23.1 μmol) was dissolved (partially suspended) in benzene (2.0 ml), and dropwise added to a benzene (2.0 ml) suspension reflux liquid of aluminium chloride (9.2 mg, 69.0 μmol). The benzene wash (8.0 ml) of the eggplant-type flask with the starting material adhering thereto was also added, followed by refluxing for 0.5 hours. After cooling, aluminium chloride (61.7 mg, 462 μmol) was further added, followed by further stirring under reflux for 15 minutes. After cooling, saturated sodium bicarbonate water (50 ml) was added to the reaction liquid, the product was extracted with chloroform (50 ml×2), ethyl acetate (50 ml).

Workup

  1. washThe benzene wash (8.0 ml) of the eggplant-type flask with the starting material adhering
  2. additionthereto was also added
  3. temperatureby refluxing for 0.5 hours
  4. temperatureAfter cooling
  5. temperatureunder reflux for 15 minutes
  6. temperatureAfter cooling
  7. extractionthe product was extracted with chloroform (50 ml×2), ethyl acetate (50 ml)

Sources & evidence

ORD record
ord-f1fbc936f0934ad7a1f753de2457b8f9
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Linked notes

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