2-Aminoindane → HCID 58276358, compound

HRID 70337Notes

Reaction equation

HRID 70337 reaction equation
[CH3:1][C:2]([CH3:27])([CH3:26])[C:3]([O:5][CH2:6][N:7]1[CH:11]=[N:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]=O)[CH:19]=3)=[CH:14][CH:13]=2)=[N:8]1)=[O:4].[NH2:28][CH:29]1[CH2:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30]1.C1COCC1.CO>C(O)(=O)C>[CH3:1][C:2]([CH3:27])([CH3:26])[C:3]([O:5][CH2:6][N:7]1[CH:11]=[N:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][NH:28][CH:29]4[CH2:37][C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[CH2:30]4)[CH:19]=3)=[CH:16][CH:17]=2)=[N:8]1)=[O:4]

Participants

5

Reactant 3

HCID 763102-AminoindaneHCID 21899815MeOH tetrahydrofuranHCID 58276410HCID 58276410, compound

Product 1

HCID 58276358HCID 58276358, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of [3-(3′-formyl-4-biphenylyl)-1H-1,2,4-triazol-1-yl]methyl 2,2-dimethylpropanoate (0.081 g, 0.22 mmol; I-X-17) and 2-aminoindane (0.045 mL, 0.35 mmol) in 1:1 THF/MeOH (2 mL) was added acetic acid (0.12 mL) and MP—BH3CN (ca. 0.67 mmol, Note 1). The mixture was stirred at room temperature overnight, resin was remove by filtration (THF wash) and the filtrate was concentrated in vacuo. The residue was partitioned between EtOAc/5% Na2CO3, layers were separated and the aqueous layer was extracted with EtOAc. Combined organics were washed (water, brine), dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography (MeOH/CH2Cl2), affording the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 1.20 (s, 9 H), 2.84 (dd, J=15.6, 6.4 Hz, 2 H), 3.20 (dd, J=15.6, 7.1 Hz, 2 H), 3.68-3.75 (m, 1 H), 3.93 (s, 2 H), 6.09 (s, 2 H), 7.08-7.23 (m, 4 H), 7.31-7.38 (m, 1 H), 7.41 (t, J=7.6 Hz, 1 H), 7.53 (d, J=7.6 Hz, 1 H), 7.63 (s, 1 H), 7.69 (d, J=8.3 Hz, 2 H), 8.19 (d, J=8.3 Hz, 2 H), 8.37 (s, 1 H).

Workup

  1. customresin was remove by filtration (THF wash)
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was partitioned between EtOAc/5% Na2CO3, layers
  4. customwere separated
  5. extractionthe aqueous layer was extracted with EtOAc
  6. washCombined organics were washed (water, brine)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography (MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-73dbbbf537394ce184ea6d8a98a5a143
Source dataset
uspto-grants-2014_09
Patent number
US08822518B2

Reaction notes

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