Oxalyl chloride → HCID 178480685, 화합물

HRID 1487407

반응식

HRID 1487407 반응식
C(Cl)(=O)C(Cl)=O.[CH3:7][N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[C:16]([N:23]([CH:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])[CH:15]=2)[CH2:10][CH2:9]1.[F:36][C:37]1[CH:38]=[C:39]([S:44][C:45]2[CH:46]=[C:47]3[C:53]([NH2:54])=[N:52][NH:51][C:48]3=[N:49][CH:50]=2)[CH:40]=[C:41]([F:43])[CH:42]=1.C(N(C(C)C)C(C)C)C>CN(C)C=O.ClCCl.C1(C)C=CC=CC=1.O1CCCC1>[F:36][C:37]1[CH:38]=[C:39]([S:44][C:45]2[CH:46]=[C:47]3[C:53]([NH:54][C:18](=[O:20])[C:17]4[CH:21]=[CH:22][C:14]([N:11]5[CH2:10][CH2:9][N:8]([CH3:7])[CH2:13][CH2:12]5)=[CH:15][C:16]=4[N:23]([CH:30]4[CH2:31][CH2:32][O:33][CH2:34][CH2:35]4)[C:24](=[O:29])[C:25]([F:26])([F:27])[F:28])=[N:52][NH:51][C:48]3=[N:49][CH:50]=2)[CH:40]=[C:41]([F:43])[CH:42]=1

참가 물질

9

반응물 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 46928120HCID 46928120, 화합물HCID 178509236HCID 178509236, 화합물

생성물 1

HCID 178480685HCID 178480685, 화합물수율 53%

시약·촉매·용매 4

HCID 6228Dimethylformamide촉매HCID 1140Toluene용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

실험 절차

0.95 ml (11.21 mmol) of oxalyl chloride and 2 drops of anhydrous dimethylformamide are added to 2.97 g (5.61 mmol) of a solution of 4-(4-methylpiperazin-1-yl)-2-(2,2,2-trifluoro-N-(tetrahydro-2H-pyran-4-yl)acetamido)benzoic acid in 95 ml of dichloromethane. The reaction mixture is stirred for 2 hours at room temperature. The solvents are evaporated, the solid formed is taken up in toluene and the solvent evaporated. This operation is repeated three times until a white solid is obtained. The acid chloride is dissolved in 35 ml of anhydrous tetrahydrofuran at −20° C. and then the solution formed is added to a solution containing 1.56 g (5.61 mmol) of 5-(3,5-difluorophenylthio)-1H-pyrazolo[3,4-b]pyridin-3-amine and 3.71 ml (21.30 mmol) of N-ethyl-N-isopropylpropan-2-amine in 30 ml of anhydrous tetrahydrofuran. The reaction mixture is stirred for 3 hours at −20° C. and then overnight at room temperature. The precipitate obtained is filtered and rinsed with tetrahydrofuran and water and then dried to yield 2 g (53%) of N-(5-(3,5-difluorophenylthio)-1H-pyrazolo[3,4-b]pyridin-3-yl)-4-(4-methylpiperazin-1-yl)-2-(2,2,2-trifluoro-N-(tetrahydro-2H-pyran-4-yl) acetamido)benzamide.

후처리

  1. customThe solvents are evaporated
  2. customthe solid formed
  3. customthe solvent evaporated
  4. customis obtained
  5. customthe solution formed
  6. additionis added to a solution
  7. stirringThe reaction mixture is stirred for 3 hours at −20° C.
  8. customovernight
  9. customat room temperature
  10. customThe precipitate obtained
  11. filtrationis filtered
  12. washrinsed with tetrahydrofuran and water
  13. customdried

출처 및 근거

ORD 기록
ord-3043b62f7eff423482b67d88257c434f
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428510B2

연결된 노트

불러오는 중…