Dimethyl Sulfoxide → HCID 68585578, compound

HRID 17604Notes

Reaction equation

HRID 17604 reaction equation
CS(C)=O.F[C:6]1[C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:8]([CH3:21])[C:9]([C:19]#[N:20])=[C:10]2[C:14]=1[O:13][C:12]([C:15]([F:18])([CH3:17])[CH3:16])=[N:11]2.C(N(CC)CC)C.[CH3:35][N:36]([CH3:42])[C@H:37]1[CH2:41][CH2:40][NH:39][CH2:38]1>[Cl-].[Na+].O>[CH3:35][N:36]([CH3:42])[C@H:37]1[CH2:41][CH2:40][N:39]([C:6]2[C:7]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:8]([CH3:21])[C:9]([C:19]#[N:20])=[C:10]3[C:14]=2[O:13][C:12]([C:15]([F:18])([CH3:17])[CH3:16])=[N:11]3)[CH2:38]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 68585577HCID 68585577, compound

Product 1

HCID 68585578HCID 68585578, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

Under nitrogen atmosphere, a dimethyl sulfoxide (4 ml) solution of 7-fluoro-2-(1-fluoro-1-methylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-312) (128 mg, 410 μmol), triethylamine (74 μl, 533 μmol) and (3S)-3-(dimethylamino)pyrrolidine (62 μl, 492 μmol) was stirred at 90° C. for 2.5 hours. After cooling, saturated-brine was added to the reaction liquid, and the mixture liquid was extracted with ethyl acetate. Next, the combined organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by middle-pressure liquid chromatography (eluent, dichloromethane:methanol=10:1, v/v) to obtain a rough product of the entitled compound, followed by suspension washing with diethyl ether to obtain the entitled compound as a pale yellow solid. The filtrate was concentrated, and the obtained solid was washed by suspension with isopropyl ether to obtain the entitled compound as a pale yellow solid (total 54 mg, 38%).

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture liquid was extracted with ethyl acetate
  3. dry with materialNext, the combined organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by middle-pressure liquid chromatography (eluent, dichloromethane
  7. custommethanol=10:1, v/v) to obtain a rough product of the entitled compound
  8. washwashing with diethyl ether

Sources & evidence

ORD record
ord-6b4ba1f448bc46bc9bbbc54ea5cb9937
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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