(+-)-1-Aminoindan → HCID 68516404, compound

HRID 2094829Notes

Reaction equation

HRID 2094829 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:42]1([NH2:51])[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH2:44][CH2:43]1>CC(N(C)C)=O>[CH:42]1([NH:51][C:5](=[O:7])[C:4]2[CH:8]=[CH:9][C:10]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)=[CH:11][C:3]=2[O:2][CH3:1])[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH2:44][CH2:43]1

Participants

5

Reactant 3

HCID 123445(+-)-1-AminoindanHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 46315946HCID 46315946, compound

Product 1

HCID 68516404HCID 68516404, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent4×

Procedure

To a solution of 2-methoxy-4-(pyridin-4-yl)benzoic acid (34 mg, 0.15 mmol), dissolved in DMA (0.5 ml) was added a solution of HATU (68 mg, 0.18 mmol) dissolved in DMA (0.5 ml). Then a solution of TEA (55 mg, 0.5 mmol), dissolved in DMA (0.4 ml) was added, followed by a solution of 2,3-dihydro-1H-inden-1-amine (27 mg, 0.2 mmol) dissolved in DMA (0.7 ml). The resulting mixture was shaken for 4 hours at room temperature. The reaction was checked by LC/MS and concentrated to dryness. The residue was dissolved in 1:1 DMSO/methanol and purified by reverse phase HPLC (TFA method) to afford the title compound.

Workup

  1. additionwas added
  2. concentrationconcentrated to dryness
  3. dissolutionThe residue was dissolved in 1:1 DMSO/methanol
  4. custompurified by reverse phase HPLC (TFA method)

Sources & evidence

ORD record
ord-2246bbf3f3114f028fec39e4769a4ce4
Source dataset
uspto-grants-2013_05
Patent number
US08445686B2

Reaction notes

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