Formic Acid → HCID 24178417, compound

HRID 218339Notes

Reaction equation

HRID 218339 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].[CH:30]([OH:32])=[O:31]>CO>[CH:30]([OH:32])=[O:31].[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 284Formic AcidHCID 6918554Indacaterol

Product 1

HCID 24178417HCID 24178417, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 2.00 g (R)-5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one base (5.1 mmoles) in 15 ml methanol is heated to 50° C. 0.24 g formic acid (5.2 mmoles) are dropwise added. The dropping funnel is rinsed with 5 ml methanol. The resulting clear solution is allowed to slowly cool. Crystallization starts spontaneously at ca. 47° C. The mixture is stirred at ca. 25° c. for 15 hours and filtered. The filter cake is washed with 4 ml methanol. The salt is dried for 20 hours at 50° C./ca. 10 mbar and for 3 hours at 70° C. and ca. 1 mbar. Yield: 1.77 g white powder (79.37%)

Workup

  1. washThe dropping funnel is rinsed with 5 ml methanol
  2. temperatureto slowly cool
  3. customCrystallization
  4. customstarts spontaneously at ca. 47° C
  5. filtrationfiltered
  6. washThe filter cake is washed with 4 ml methanol
  7. customThe salt is dried for 20 hours at 50° C./ca. 10 mbar
  8. waitfor 3 hours at 70° C.

Sources & evidence

ORD record
ord-cbff3bd52aae4ccd8d9dca8ca4d6d649
Source dataset
uspto-grants-2012_06
Patent number
US08198450B2

Reaction notes

Loading…