p-Toluenesulfonic acid monohydrate → HCID 24178419, compound

HRID 218340Notes

Reaction equation

HRID 218340 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].O.[C:31]1([CH3:41])[CH:36]=[CH:35][C:34]([S:37]([OH:40])(=[O:39])=[O:38])=[CH:33][CH:32]=1>C(OC(=O)C)C>[S:37]([C:34]1[CH:35]=[CH:36][C:31]([CH3:41])=[CH:32][CH:33]=1)([OH:40])(=[O:39])=[O:38].[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 521998p-Toluenesulfonic acid monohydrateHCID 6918554Indacaterol

Product 1

HCID 24178419HCID 24178419, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture 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) and 0.98 g p-toluenesulfonic acid monohydrate (5.1 mmoles) in 30 ml ethylacetate is heated to 60° C. During heating the initially sticky yellow amorphous mass, turns to a white, good stirrable suspension. The suspension is allowed to cool and stirred at room temperature over night. The crystals are collected after filtration and washing with ethylacetate. The salt is dried for ca. 20 hours at 50° C. and ca. 10 mbar. Yield: 2.73 g off white powder (94.8%)

Workup

  1. temperatureDuring heating the initially sticky yellow amorphous mass
  2. temperatureto cool
  3. customThe crystals are collected
  4. filtrationafter filtration
  5. washwashing with ethylacetate
  6. customThe salt is dried for ca. 20 hours at 50° C.

Sources & evidence

ORD record
ord-1693e9727a0f4afcba12f17fbe4035c2
Source dataset
uspto-grants-2012_06
Patent number
US08198450B2

Reaction notes

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