2-Furanacrylic acid → HCID 59506943、化合物

HRID 1800531

反応式

HRID 1800531 の反応式
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[CH:6]=[CH:7]/[C:8]([OH:10])=O.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[NH2:35][C:36]1[S:37][C:38]2[C:43]([N:44]=1)=[CH:42][CH:41]=[C:40]([O:45][C:46]1[C:47]([Cl:67])=[CH:48][C:49]([F:66])=[C:50]([NH:52][C:53](=[O:65])[C:54]3[CH:59]=[CH:58][CH:57]=[C:56]([C:60]([C:63]#[N:64])([CH3:62])[CH3:61])[CH:55]=3)[CH:51]=1)[N:39]=2>N1C=CC=CC=1.C(OCC)(=O)C>[Cl:67][C:47]1[C:46]([O:45][C:40]2[N:39]=[C:38]3[S:37][C:36]([NH:35][C:8](=[O:10])/[CH:7]=[CH:6]/[C:2]4[O:1][CH:5]=[CH:4][CH:3]=4)=[N:44][C:43]3=[CH:42][CH:41]=2)=[CH:51][C:50]([NH:52][C:53](=[O:65])[C:54]2[CH:59]=[CH:58][CH:57]=[C:56]([C:60]([C:63]#[N:64])([CH3:62])[CH3:61])[CH:55]=2)=[C:49]([F:66])[CH:48]=1

参加物

6

反応物 3

HCID 6434022-Furanacrylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86646015HCID 86646015、化合物

生成物 1

HCID 59506943HCID 59506943、化合物収率 87%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (2E)-3-furan-2-ylprop-2-enoic acid (24 mg, 0.173 mmol) in pyridine (1.0 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (65.7 mg, 0.173 mmol), and the mixture was stirred at room temperature for 10 min. N-{5-[(2-Amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-chloro-2-fluorophenyl}-3-(1-cyano-1-methylethyl)benzamide (80 mg, 0.166 mmol) produced in Example C52(v) was added to the obtained solution, and the mixture was stirred at 80° C. for 12 hr. The reaction mixture was diluted with ethyl acetate (10 mL), washed with 5% aqueous sodium hydrogen carbonate solution (10 mL) and saturated brine (100 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=70/30→0/100), and the obtained solution was concentrated under reduced pressure. The residue was crystallized from ethyl acetate/hexane to give the title compound (37.2 mg, 87%) as a colorless powder.

後処理

  1. additionwas added to the obtained solution
  2. stirringthe mixture was stirred at 80° C. for 12 hr
  3. washwashed with 5% aqueous sodium hydrogen carbonate solution (10 mL) and saturated brine (100 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=70/30→0/100)
  8. concentrationthe obtained solution was concentrated under reduced pressure
  9. customThe residue was crystallized from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-083e2b5d7e304296a45e96fd5708ee06
出典データセット
uspto-grants-2013_01
特許番号
US08344135B2

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