Triethylamine → (E)-4,4,5,5,5-Pentafluoro-N-[3-[(2-methyl-4-quinolyl)amino]propyl]pent-2-enamide

HRID 333065노트

반응식

HRID 333065 반응식
[F:1][C:2]([F:12])([C:8]([F:11])([F:10])[F:9])/[CH:3]=[CH:4]/[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.Cl.[CH3:45][C:46]1[CH:55]=[C:54]([NH:56][CH2:57][CH2:58][CH2:59][NH2:60])[C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[N:47]=1.[O-2].[Al+3].[O-2].[O-2].[Al+3]>CN(C=O)C.C(#N)C>[F:12][C:2]([F:1])([C:8]([F:11])([F:10])[F:9])/[CH:3]=[CH:4]/[C:5]([NH:60][CH2:59][CH2:58][CH2:57][NH:56][C:54]1[C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[N:47]=[C:46]([CH3:45])[CH:55]=1)=[O:7]

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9989226AluminaHCID 17999421N1-(2-Methylquinolin-4-YL)propane-1,3-diamine hydrochlorideHCID 86691160(2E)-4,4,5,5,5-Pentafluoro-2-pentenoic acid

생성물 1

HCID 86691162(E)-4,4,5,5,5-Pentafluoro-N-[3-[(2-methyl-4-quinolyl)amino]propyl]pent-2-enamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매

실험 절차

(E)-4,4,5,5,5-Pentafluoropent-2-enoic acid (38 mg, 0.2 mmol) and HBTU (76 mg, 0.2 mmol) were dissolved in a 1:1 mixture of anhydrous DMF and anhydrous acetonitrile (2 ml), after 5 minutes triethylamine (82 μl, 0.6 mmol) and N-(2-methyl-4-quinolyl)propane-1,3-diamine hydrochloride (48 mg, 0.24 mmol) was added and stirring was continued for 3 hours. To the mixture basic aluminium oxide was added, stirring was continued for one hour, the mixture was filtered and the filtrate was evaporated to dryness under reduced pressure. The residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 28.4 mg (0.076 mmol, 38%).

후처리

  1. additionwas added
  2. stirringstirring
  3. waitwas continued for one hour
  4. filtrationthe mixture was filtered
  5. customthe filtrate was evaporated to dryness under reduced pressure
  6. customThe residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
  7. customto yield 28.4 mg (0.076 mmol, 38%)

출처 및 근거

ORD 기록
ord-0d5bac1625eb4331b0eff6a63b8e83d3
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877934B2

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