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Triethylamine → 7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-2-(methylamino)-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17399
Notes
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Reaction equation

HRID 17399 reaction equation
F[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:4]([CH3:15])[C:5]([C:13]#[N:14])=[C:6]2[C:10]=1[O:9][C:8]([NH:11][CH3:12])=[N:7]2.[CH2:22]([N:24]([CH2:27]C)[CH2:25][CH3:26])C.C[NH:30][C@H:31]1CCN[CH2:32]1>CS(C)=O.ClCCl>[CH3:27][N:24]([CH3:22])[C@H:25]1[CH2:32][CH2:31][N:30]([C:2]2[C:3]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:4]([CH3:15])[C:5]([C:13]#[N:14])=[C:6]3[C:10]=2[O:9][C:8]([NH:11][CH3:12])=[N:7]3)[CH2:26]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10261057(3S)-(-)-3-(Methylamino)pyrrolidineHCID 510399667-Fluoro-5-methyl-2-(methylamino)-6-phenyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 510393137-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-2-(methylamino)-6-phenyl-1,3-benzoxazole-4-carbonitrileYield 30.3%

Reagents, catalysts & solvents 2

HCID 679
Dimethyl Sulfoxide
Solvent
HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

7-Fluoro-5-methyl-2-(methylamino)-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-131) (0.17 g, 0.60 mmol) was dissolved in dimethyl sulfoxide (5 ml), then triethylamine (0.17 ml, 1.23 mmol) and (3S)-3-methylaminopyrrolidine (0.16 ml, 1.26 mmol) were added, followed by stirring in a sealed tube at an external temperature of about 150° C. for 4 hours. This was diluted with dichloromethane, washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1 to 10:1), then diisopropyl ether was added, and the insoluble matter was collected by filtration to obtain a beige solid (68.3 mg, 27%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated away under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1 to 10:1)
  5. additiondiisopropyl ether was added
  6. filtrationthe insoluble matter was collected by filtration

Sources & evidence

ORD record
ord-f6240afead2c43dd9608ba0232b53dd5
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737166B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes