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Triethylamine → 4-Cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-N-methoxy-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

HRID 17377
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HRID 17377 반응식
[C:1]([C:3]1[C:8]2[N:9]=[C:10]([C:12]([N:14]([O:16][CH3:17])[CH3:15])=[O:13])[O:11][C:7]=2[C:6](F)=[C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:4]=1[CH3:25])#[N:2].C(N(CC)CC)C.[CH3:33][N:34]([CH3:40])[C@H:35]1[CH2:39][CH2:38][NH:37][CH2:36]1.C(OCC)(=O)C>CS(C)=O.[Cl-].[Na+].O>[C:1]([C:3]1[C:8]2[N:9]=[C:10]([C:12]([N:14]([O:16][CH3:17])[CH3:15])=[O:13])[O:11][C:7]=2[C:6]([N:37]2[CH2:38][CH2:39][C@H:35]([N:34]([CH3:40])[CH3:33])[CH2:36]2)=[C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:4]=1[CH3:25])#[N:2]
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참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 866308444-Cyano-7-fluoro-N-methoxy-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

생성물 1

HCID 866308434-Cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-N-methoxy-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide수율 32%

시약·촉매·용매

2
HCID 679Dimethyl Sulfoxide용매2회HCID 57417360Sodium chloride; water용매

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온도
150 °C

실험 절차

4-Cyano-7-fluoro-N-methoxy-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide (I-115) (200 mg, 0.59 mmol) was dissolved in dimethyl sulfoxide (10 ml), and at room temperature, triethylamine (99 μl, 0.71 mmol) was added. Next, the solution was heated at 150° C., and a solution of (3S)-3-(dimethylamino)pyrrolidine (90 μl, 0.71 mmol) dissolved in dimethyl sulfoxide (2 ml) was added all at a time, followed by further stirring for 1.5 hours. 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=94:6) to obtain the entitled compound (81 mg, 32%) as a brown amorphous substance.

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=94:6)

출처 및 근거

ORD 기록
ord-a52a6c40149e41aca560ea978f27c651
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07737166B2

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