Triethylamine → tert-Butyl (1-{4-Cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}azetidin-3-yl)carbamate

HRID 17486노트

반응식

HRID 17486 반응식
[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]([N:27]3[CH2:30][CH:29]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:28]3)[O:26][C:22]=2[C:21](F)=[C:20]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:19]=1[CH3:46])#[N:17]>CS(C)=O>[C:16]([C:18]1[C:23]2[N:24]=[C:25]([N:27]3[CH2:28][CH:29]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:30]3)[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:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:19]=1[CH3:46])#[N:17]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 86630856HCID 86630856, 화합물

생성물 1

HCID 86630855tert-Butyl (1-{4-Cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}azetidin-3-yl)carbamate수율 53.2%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
130 °C

실험 절차

(3S)-3-(Dimethylamino)pyrrolidine (180 μl, 1.42 mmol) and triethylamine (238 μl, 1.70 mmol) were added to a dimethyl sulfoxide (5 ml) solution of tert-butyl [1-(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)azetidin-3-yl]carbamate (I-194) (400 mg, 0.947 mmol), followed by stirring in an oil bath at 130° C. for 3 hours. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in chloroform (100 ml) and washed with saturated brine (100 ml). After drying over anhydrous sodium sulfate and concentration, the resulting residue was purified by silica gel column chromatography (eluent, chloroform:methanol=10:1) to obtain the entitled compound (260 mg, 53.2%) as a colorless solid.

후처리

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform (100 ml)
  4. washwashed with saturated brine (100 ml)
  5. dry with materialAfter drying over anhydrous sodium sulfate and concentration
  6. customthe resulting residue was purified by silica gel column chromatography (eluent, chloroform:methanol=10:1)

출처 및 근거

ORD 기록
ord-4a503bc31ad34059bd55bccb28d68930
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

반응 노트

불러오는 중…