2-Furanacrylic acid → HCID 59506943, compound

HRID 1800531

Reaction equation

HRID 1800531 reaction equation
[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

Participants

6

Reactant 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, compound

Product 1

HCID 59506943HCID 59506943, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-083e2b5d7e304296a45e96fd5708ee06
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Linked notes

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