Ammonium Bicarbonate → 5-[(R)-2-(2-{4-[4-(2-amino-2-methyl-propoxy)-phenylamino]-phenyl}-ethylamino)-1-hydroxy-ethyl]-8-hydroxy-1H-quinolin-2-one

HRID 1670801Notes

Reaction equation

HRID 1670801 reaction equation
C(=O)(O)[O-].[NH4+].FC(F)(F)C([O-])=O.FC(F)(F)C(O)=O.[NH2:20][C:21]([CH3:56])([CH3:55])[CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][NH:39][CH2:40][C@@H:41]([C:43]3[CH:52]=[CH:51][C:50]([OH:53])=[C:49]4[C:44]=3[CH:45]=[CH:46][C:47](=[O:54])[NH:48]4)[OH:42])=[CH:33][CH:32]=2)=[CH:26][CH:25]=1>C(O)C>[NH2:20][C:21]([CH3:56])([CH3:55])[CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]2[CH:32]=[CH:33][C:34]([CH2:37][CH2:38][NH:39][CH2:40][C@@H:41]([C:43]3[CH:52]=[CH:51][C:50]([OH:53])=[C:49]4[C:44]=3[CH:45]=[CH:46][C:47](=[O:54])[NH:48]4)[OH:42])=[CH:35][CH:36]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 14013Ammonium BicarbonateHCID 84468TrifluoroacetateHCID 865997215-[(R)-2-(2-{4-[4-(2-amino-2-methyl-propoxy)-phenylamino]-phenyl}-ethylamino)-1-hydroxy-ethyl]-8-hydroxy-1H-quinolin-2-one trifluoroacetate

Product 1

HCID 111693655-[(R)-2-(2-{4-[4-(2-amino-2-methyl-propoxy)-phenylamino]-phenyl}-ethylamino)-1-hydroxy-ethyl]-8-hydroxy-1H-quinolin-2-oneYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Aqueous ammonium bicarbonate (10%) solution (50 mL) was added in one portion to a solution of the product of Example 1, 5-[(R)-2-(2-{4-[4-(2-amino-2-methyl-propoxy)-phenylamino]-phenyl}-ethylamino)-1-hydroxy-ethyl]-8-hydroxy-1H-quinolin-2-one trifluoroacetate, (1.80 g, 2.1 mmol) in ethanol (6 mL). The solution was stirred at room temperature for 1 h. The resultant solid was filtered and dried under reduced pressure to afford the title compound (0.84 g, 1.67 mmol, 80%) as a yellow solid.

Workup

  1. filtrationThe resultant solid was filtered
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-f3de64ba23ec4ee58b6e32ae33097275
Source dataset
uspto-grants-2011_08
Patent number
US07994165B2

Reaction notes

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