4-methoxythiophene-3-carboxylic acid → HCID 44540247, compound

HRID 244734Notes

Reaction equation

HRID 244734 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:8]([OH:10])=O)=[CH:5][S:6][CH:7]=1.F[P-](F)(F)(F)(F)F.CN(C(ON1C2=NC=CC=C2N=N1)=[N+](C)C)C.[NH:35]1[C:43]2[C:38](=[C:39]([C:44]3[CH:45]=[C:46]([NH2:53])[C:47]4[CH:48]=[N:49][NH:50][C:51]=4[CH:52]=3)[CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36]1>CN(C=O)C.CCN(C(C)C)C(C)C>[NH:35]1[C:43]2[C:38](=[C:39]([C:44]3[CH:52]=[C:51]4[C:47]([CH:48]=[N:49][NH:50]4)=[C:46]([NH:53][C:8]([C:4]4[C:3]([O:2][CH3:1])=[CH:7][S:6][CH:5]=4)=[O:10])[CH:45]=3)[CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36]1

Participants

6

Reactant 3

HCID 27783794-methoxythiophene-3-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 582680196-(1H-indol-4-yl)-1H-indazol-4-amine

Product 1

HCID 44540247HCID 44540247, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

4-(Methyloxy)-3-thiophenecarboxylic acid (35 mg) was treated with N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethanaminium hexafluorophosphate (84 mg) in DMF (250 μl) and DIPEA (69 μl). The reaction mixture was shaken for five min prior to treatment with 6-(1H-indol-4-yl)-1H-indazol-4-amine (25 mg) in DMF (250 μl). The reaction mixture was left to stand at 22° C. for 18 h. The solvent was removed in vacuo and the product re-dissolved in chloroform (0.3 ml) prior to application on to an aminopropyl SPE cartridge (0.5 g) that had been preconditioned with methanol and then chloroform. The product was eluted after 2 hr with ethyl acetate/methanol (1:1, 3 ml), and concentrated under a stream of nitrogen using blow down apparatus. Purification by mass directed preparative HPLC (Method C) gave the title compound.

Workup

  1. waitThe reaction mixture was left
  2. waitto stand at 22° C. for 18 h
  3. customThe solvent was removed in vacuo
  4. dissolutionthe product re-dissolved in chloroform (0.3 ml)
  5. washThe product was eluted after 2 hr with ethyl acetate/methanol (1:1, 3 ml)
  6. concentrationconcentrated under a stream of nitrogen using blow down apparatus
  7. customPurification by mass

Sources & evidence

ORD record
ord-030c54546ca744bd89c0909c47ab224a
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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