HCID 86724256, compound → HCID 86724293, compound

HRID 873745Notes

Reaction equation

HRID 873745 reaction equation
[CH3:1][O:2][CH2:3][C:4]#[C:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:13]=[C:14]3[C:41](=[CH:42][CH:43]=2)[O:40][CH2:39][C:35]2([CH2:38][O:37][CH2:36]2)[C:15]23[CH2:19][O:18][C:17]([N:20](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=[N:16]2)[CH:9]=[N:10][CH:11]=1>C1(C)C=CC=CC=1>[CH3:1][O:2][CH2:3][C:4]#[C:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:13]=[C:14]3[C:41](=[CH:42][CH:43]=2)[O:40][CH2:39][C:35]2([CH2:38][O:37][CH2:36]2)[C:15]23[CH2:19][O:18][C:17]([NH2:20])=[N:16]2)[CH:9]=[N:10][CH:11]=1

Participants

3

Reactant 1

HCID 86724256HCID 86724256, compound

Product 1

HCID 86724293HCID 86724293, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of di-tert-butyl {6′-[5-(3-methoxyprop-1-yn-1-yl)pyridin-3-yl]dispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-yl}imidodicarbonate (220 mg, 0.372 mmol), silica gel (neutral; 660 mg) and toluene (2.2 mL) was stirred for 3 hours at 100° C. The mixture was cooled down to ambient temperature, and concentrated at reduced pressure. Purification of the residue with column chromatography on silica gel (CHCl3-MeOH, a linear gradient of MeOH from 0 to 10%) afforded 6′-[5-(3-methoxyprop-1-yn-1-yl)pyridin-3-yl]dispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-amine (92.4 mg).

Workup

  1. temperatureThe mixture was cooled down to ambient temperature
  2. concentrationconcentrated at reduced pressure
  3. customPurification of the residue with column chromatography on silica gel (CHCl3-MeOH

Sources & evidence

ORD record
ord-51482eff2f524ac8b9a7e33c51dea3eb
Source dataset
uspto-grants-2015_03
Patent number
US08975415B2

Reaction notes

Loading…