Glycolic Acid → HCID 24178423, compound

HRID 218341Notes

Reaction equation

HRID 218341 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].[C:30]([OH:34])(=[O:33])[CH2:31][OH:32]>CO>[C:30]([OH:34])(=[O:33])[CH2:31][OH:32].[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 757Glycolic AcidHCID 6918554Indacaterol

Product 1

HCID 24178423HCID 24178423, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
50 °C

Procedure

A suspension of 2.075 g (R)-5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one base (5.286 mmoles) in 25 ml methanol is heated to 50° C. A solution of 0.402 g glycolic acid (5.286 mmoles) in 5 ml methanol is added dropwise over 7 minutes. The resulting clear solution is stirred at 50° C. Crystallization takes spontaneously place after ca 15 minutes. The white suspension is allowed to cool to room temperature and stirred over night at ca. 25° C. After 18 hours the salt is filtered. The filter cake is washed with 7 ml methanol and dried first 20 hours at 60° C. and ca. 10 mbar and then 2 hours at 60° C. and ca. 1 mbar.

Workup

  1. customCrystallization
  2. customafter ca 15 minutes
  3. temperatureto cool to room temperature
  4. stirringstirred over night at ca. 25° C
  5. filtrationAfter 18 hours the salt is filtered
  6. washThe filter cake is washed with 7 ml methanol
  7. customdried first 20 hours at 60° C.
  8. custom2 hours
  9. customat 60° C.

Sources & evidence

ORD record
ord-4bad1e73354443a6b28a1f42af23013b
Source dataset
uspto-grants-2012_06
Patent number
US08198450B2

Reaction notes

Loading…