Triethylamine → Ethyl-4-cyano-7-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate

HRID 17368

반응식

HRID 17368 반응식
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[C:14](F)=[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:12]([CH3:22])=[C:11]([C:23]#[N:24])[C:9]=2[N:10]=1)=[O:5])[CH3:2].C(N(CC)CC)C.[CH3:32][N:33]([CH3:39])[C@H:34]1[CH2:38][CH2:37][NH:36][CH2:35]1.C(OCC)(=O)C>CS(C)=O.[Cl-].[Na+].O>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[C:14]([N:36]3[CH2:37][CH2:38][C@H:34]([N:33]([CH3:39])[CH3:32])[CH2:35]3)=[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:12]([CH3:22])=[C:11]([C:23]#[N:24])[C:9]=2[N:10]=1)=[O:5])[CH3:2]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 51041426Ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate

생성물 1

HCID 51041664Ethyl-4-cyano-7-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate수율 7%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회HCID 57417360Sodium chloride; water용매

반응 조건

온도
150 °C

실험 절차

Ethyl-4-cyan-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate 111) (200 mg, 0.62 mmol) was dissolved in dimethyl sulfoxide (12 ml), and at room temperature, triethylamine (112 μl, 0.80 mmol) was added. Next, the solution was heated at 150° C., and a solution of (3S)-3-(dimethylamino)pyrrolidine (94 μl, 0.74 mmol) dissolved in dimethyl sulfoxide (2 ml) was added all at a time, followed by further stirring for 1 hour. The mixture liquid was cooled to room temperature, then this was fractionated with ethyl acetate and saturated brine. The aqueous layer was separated, this was extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=98:2) to obtain the entitled compound (17.5 mg, 7%) as a yellow powdery crystal.

후처리

  1. additionwas added all at a time
  2. temperatureThe mixture liquid was cooled to room temperature
  3. customThe aqueous layer was separated
  4. extractionthis was extracted twice with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe insoluble matter was separated by filtration
  8. customthe solvent was evaporated away
  9. customthe resulting residue was purified by preparative TLC (eluent, chloroform:methanol=98:2)

출처 및 근거

ORD 기록
ord-f2015a023d4a485db0465b7f7b524891
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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