Triethylamine → Ethyl 4-({4-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}amino)butanoate

HRID 17568Notes

Reaction equation

HRID 17568 reaction equation
[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.C(N(CC)CC)C.[C:16]([C:18]1[C:23]2[N:24]=[C:25]([NH:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[O:26][C:22]=2[C:21](F)=[C:20]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:19]=1[CH3:43])#[N:17]>CS(C)=O>[C:16]([C:18]1[C:23]2[N:24]=[C:25]([NH:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[O:26][C:22]=2[C:21]([N:5]2[CH2:6][CH2:7][C@H:3]([N:2]([CH3:8])[CH3:1])[CH2:4]2)=[C:20]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:19]=1[CH3:43])#[N:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 51039317Ethyl 4-[(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)amino]butanoate

Product 1

HCID 51041665Ethyl 4-({4-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}amino)butanoateYield 49%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

(3S)-3-(Dimethylamino)pyrrolidine (139 μl, 1.10 mmol) and triethylamine (153 μl, 1.10 mmol) were added to a dimethyl sulfoxide (5 ml) solution of ethyl 4-[(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)amino]butanoate (I-280) (279 mg, 0.732 mmol), followed by stirring in an oil bath at 150° C. for 5 hours. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in chloroform and washed with saturated brine. After drying over anhydrous sodium sulfate, the insoluble matter was separated by filtration, the residue obtained by concentration was purified by silica gel column chromatography (eluent, chloroform:methanol=10:1, v/v) to obtain the entitled compound (170 mg, 49%) as a brown oily substance.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform
  4. washwashed with saturated brine
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. customthe insoluble matter was separated by filtration
  7. customthe residue obtained by concentration
  8. customwas purified by silica gel column chromatography (eluent, chloroform

Sources & evidence

ORD record
ord-238548e9ef514573ac3052a051c56683
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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