Triethylamine → HCID 68584875, compound

HRID 17425Notes

Reaction equation

HRID 17425 reaction equation
[C:1]([C:3]1[C:8]2[N:9]=[C:10]([N:12]([CH3:21])[CH2:13][CH2:14][CH2:15][C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[O:11][C:7]=2[C:6](F)=[C:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:4]=1[CH3:29])#[N:2].C(N(CC)CC)C.[CH3:37][N:38]([CH3:44])[C@H:39]1[CH2:43][CH2:42][NH:41][CH2:40]1>CS(C)=O.ClCCl>[C:1]([C:3]1[C:8]2[N:9]=[C:10]([N:12]([CH3:21])[CH2:13][CH2:14][CH2:15][C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[O:11][C:7]=2[C:6]([N:41]2[CH2:42][CH2:43][C@H:39]([N:38]([CH3:44])[CH3:37])[CH2:40]2)=[C:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:4]=1[CH3:29])#[N:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685844064-[{4-Cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}(methyl)amino]-N,N-dimethylbutanamide

Product 1

HCID 68584875HCID 68584875, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

4-[{4-Cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}(methyl)amino]-N,N-dimethylbutanamide (I-156) (0.32 g, 0.81 mmol) was dissolved in dimethyl sulfoxide (5 ml), then triethylamine (0.24 ml, 1.73 mmol) and (3S)-3-(dimethylamino)pyrrolidine (0.21 ml, 1.66 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, and washed with water and brine. After drying 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 colorless solid (0.22 g, 56%).

Workup

  1. washwashed with water and brine
  2. dry with materialAfter drying 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-748c846b7c284a6c93517e599349c424
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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