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

HRID 333065ノート

反応式

HRID 333065 の反応式
[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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6342Acetonitrile溶媒

実験手順

(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%).

後処理

  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%)

出典と根拠

ORDレコード
ord-0d5bac1625eb4331b0eff6a63b8e83d3
出典データセット
uspto-grants-2014_11
特許番号
US08877934B2

反応ノート

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