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

HRID 1747565Notes

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

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

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

Sources & evidence

ORD record: ord-0141cf9f19a84c20bbf6093d7033d87d
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150525B2

Reaction notes

Loading…