1-Aminoindane, (S)- → HCID 66797856, compound

HRID 447572

Reaction equation

HRID 447572 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]2[C@@H:13]3[O:14][C:15]([CH3:18])([CH3:17])[O:16][C@@H:12]3[C@@H:11]([CH2:19][OH:20])[CH2:10]2)[CH:3]=1.[NH2:21][C@@H:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][CH2:23]1>C(Cl)Cl>[C@@H:22]1([NH:21][C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]3[C@@H:13]4[O:14][C:15]([CH3:18])([CH3:17])[O:16][C@@H:12]4[C@@H:11]([CH2:19][OH:20])[CH2:10]3)[CH:3]=2)[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 70000841-Aminoindane, (S)-HCID 59671267HCID 59671267, compound

Product 1

HCID 66797856HCID 66797856, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of {(3aR,4R,6R,6aS)-6-[(6-chloropyrimidin-4-yl)amino]-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl}methanol (200 mg, 0.667 mmol) and (S)-(+)-1-aminoindan (0.188 mL, 1.47 mmol) were heated to 180° C. for 3 h in a sealed tube using MWI. The mixture was dissolved in DCM and the resulting suspension was washed with H2O followed by saturated ammonium chloride solution. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified via silica gel chromatography eluting with a gradient of 0 to 10% MeOH in EtOAc to afford the title compound as an amorphous solid (218 mg, 82.4%). LC/MS: Rt=1.44 min, ES+ 397 (AA standard).

Workup

  1. washthe resulting suspension was washed with H2O
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via silica gel chromatography
  6. washeluting with a gradient of 0 to 10% MeOH in EtOAc

Sources & evidence

ORD record
ord-c33b090479fa4d97a4598470e26847d5
Source dataset
uspto-grants-2013_07
Patent number
US08481550B2

Linked notes

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