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

HRID 17402
Notes
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Reaction equation

HRID 17402 reaction equation
F[C:2]1[C:3]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:4]([CH3:16])[C:5]([C:14]#[N:15])=[C:6]2[C:10]=1[O:9][C:8]([N:11]([CH3:13])[CH3:12])=[N:7]2.C(N(CC)CC)C.[CH3:30][N:31]([CH3:37])[C@H:32]1[CH2:36][CH2:35][NH:34][CH2:33]1>CS(C)=O.ClCCl>[CH3:12][N:11]([CH3:13])[C:8]1[O:9][C:10]2[C:6](=[C:5]([C:14]#[N:15])[C:4]([CH3:16])=[C:3]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:2]=2[N:34]2[CH2:35][CH2:36][C@H:32]([N:31]([CH3:37])[CH3:30])[CH2:33]2)[N:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685846257-Fluoro-2-(dimethylamino)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 510393142-(dimethylamino)-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrileYield 33%

Reagents, catalysts & solvents 2

HCID 679
Dimethyl Sulfoxide
Solvent
HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

7-Fluoro-2-(dimethylamino)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-132) (0.18 g, 0.61 mmol) was suspended in dimethyl sulfoxide (5 ml), then triethylamine (0.17 ml, 1.23 mmol) and (3S)-3-(dimethylamino)pyrrolidine (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=30:1), then diisopropyl ether was added, and the insoluble matter was collected by filtration to obtain a pale beige solid (78.5 mg, 33%).

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=30:1)
  5. additiondiisopropyl ether was added
  6. filtrationthe insoluble matter was collected by filtration

Sources & evidence

ORD record
ord-b45f8c6ea219484faa12f8677fab6b29
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