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

HRID 17571Notes

Reaction equation

HRID 17571 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.CS(C)=O.F[C:21]1[C:22]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[C:23]([CH3:38])[C:24]([C:36]#[N:37])=[C:25]2[C:29]=1[O:28][C:27]([N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)=[N:26]2>C(Cl)(Cl)Cl>[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][N:5]([C:21]2[C:22]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[C:23]([CH3:38])[C:24]([C:36]#[N:37])=[C:25]3[C:29]=2[O:28][C:27]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[N:26]3)[CH2:4]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685844347-Fluoro-5-methyl-2-morpholin-4-yl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 685845337-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-2-morpholin-4-yl-6-phenyl-1,3-benzoxazole-4-carbonitrileYield 22.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
150 °C

Procedure

(3S)-3-(Dimethylamino)pyrrolidine (55 μl, 0.435 mmol) and triethylamine (70 μl, 0.502 mmol) were added to a dimethyl sulfoxide (3 ml) solution of 7-fluoro-5-methyl-2-morpholin-4-yl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-283) (113 mg, 0.335 mmol), followed by stirring in an oil bath at 150° C. for 2 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 preparative TLC (eluent, chloroform:methanol=10:1, v/v), and the obtained eluate was recrystallized from hot ethanol to obtain the entitled compound (33.0 mg, 22%) as a white solid.

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. custommethanol=10:1, v/v), and the obtained eluate was recrystallized from hot ethanol

Sources & evidence

ORD record
ord-ea5ff3ad25764afa8d7c27d50a1bc979
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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