1-Aminoindane, (S)- → HCID 66797896, compound

HRID 447582Notes

Reaction equation

HRID 447582 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]2[CH2:13][C@H:12]([OH:14])[C@@H:11]([CH2:15][OH:16])[CH2:10]2)[CH:3]=1.[NH2:17][C@@H:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19]1>C(O)CCC>[C@@H:18]1([NH:17][C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]3[CH2:13][C@H:12]([OH:14])[C@@H:11]([CH2:15][OH:16])[CH2:10]3)[CH:3]=2)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 70000841-Aminoindane, (S)-HCID 59671414HCID 59671414, compound

Product 1

HCID 66797896HCID 66797896, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of (1S,2R,4R)-4-[(6-chloropyrimidin-4-yl)amino]-2-(hydroxymethyl)cyclopentanol (500. mg, 2.05 mmol), 1-butanol (4.00 mL) and (S)-(+)-1-aminoindan (0.806 mL, 6.16 mmol) was heated to 200° C. for 90 min in a sealed tube using MWI. The mixture was concentrated in vacuo and purified via silica gel chromatography eluting with a gradient of 5 to 25% MeOH in DCM to afford the title compound as an amorphous solid (513 mg, 73%). LC/MS: Rt=1.20 min, ES+ 341 (AA standard).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified via silica gel chromatography
  3. washeluting with a gradient of 5 to 25% MeOH in DCM

Sources & evidence

ORD record
ord-26063974e63d41be8defa7f186face64
Source dataset
uspto-grants-2013_07
Patent number
US08481550B2

Reaction notes

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