Hydrogen Bromide → HCID 68876933, compound

HRID 218338Notes

Reaction equation

HRID 218338 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[CH2:12][CH3:13])[CH2:8][CH:7]([NH:14][CH2:15][C@@H:16]([C:18]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]3[C:19]=1[CH:20]=[CH:21][C:22](=[O:29])[NH:23]3)[OH:17])[CH2:6]2)[CH3:2].[BrH:30]>CO>[BrH:30].[CH2:12]([C:11]1[CH:10]=[C:9]2[C:5](=[CH:4][C:3]=1[CH2:1][CH3:2])[CH2:6][CH:7]([NH:14][CH2:15][C@@H:16]([C:18]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]3[C:19]=1[CH:20]=[CH:21][C:22](=[O:29])[NH:23]3)[OH:17])[CH2:8]2)[CH3:13]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 6918554Indacaterol

Product 1

HCID 68876933HCID 68876933, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Conditions

Temperature
50 °C

Procedure

A suspension of 1.93 g (R)-5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one base (4.92 mmoles) in 13.5 ml methanol is heated to 50° C., A solution of 0.829 g hydrobromic acid 48% (4.92 mmoles) in 5 ml methanol is dropwise added over 15 minutes. The resulting very thick suspension is diluted with 43 ml methanol and allowed to cool. After stirring for 3 hours at room temperature the precipitate is filtered. The filter cake is washed with 5 ml methanol. The crystals are dried for 16 hours at 50° C./ca. 10 mbar and for 2 hours at 50° C. and ca. 1 mbar. Yield: 2.33 g white powder (84.27%)

Workup

  1. temperatureto cool
  2. filtrationis filtered
  3. washThe filter cake is washed with 5 ml methanol
  4. customThe crystals are dried for 16 hours at 50° C./ca. 10 mbar
  5. waitfor 2 hours at 50° C.

Sources & evidence

ORD record
ord-8f850db9dc4e4842a82b1336e1addc07
Source dataset
uspto-grants-2012_06
Patent number
US08198450B2

Reaction notes

Loading…