4-Methoxy cinnamic acid → 5-[(R)-2-(2-{4-[4-(2-amino-2-methyl-propoxy)-phenylamino]-phenyl}-ethylamino)-1-hydroxy-ethyl]-8-hydroxy-1H-quinolin-2-one 4-methoxy cinnamate

HRID 500980Notes

Reaction equation

HRID 500980 reaction equation
[NH2:1][C:2]([CH3:37])([CH3:36])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][NH:20][CH2:21][C@@H:22]([C:24]3[CH:33]=[CH:32][C:31]([OH:34])=[C:30]4[C:25]=3[CH:26]=[CH:27][C:28](=[O:35])[NH:29]4)[OH:23])=[CH:14][CH:13]=2)=[CH:7][CH:6]=1.[CH3:38][O:39][C:40]1[CH:50]=[CH:49][C:43]([CH:44]=[CH:45][C:46]([OH:48])=[O:47])=[CH:42][CH:41]=1>O1CCCC1>[CH3:38][O:39][C:40]1[CH:50]=[CH:49][C:43]([CH:44]=[CH:45][C:46]([OH:48])=[O:47])=[CH:42][CH:41]=1.[NH2:1][C:2]([CH3:37])([CH3:36])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][NH:20][CH2:21][C@@H:22]([C:24]3[CH:33]=[CH:32][C:31]([OH:34])=[C:30]4[C:25]=3[CH:26]=[CH:27][C:28](=[O:35])[NH:29]4)[OH:23])=[CH:16][CH:17]=2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 132454-Methoxy cinnamic acidHCID 111693655-[(R)-2-(2-{4-[4-(2-amino-2-methyl-propoxy)-phenylamino]-phenyl}-ethylamino)-1-hydroxy-ethyl]-8-hydroxy-1H-quinolin-2-one

Product 1

HCID 684588975-[(R)-2-(2-{4-[4-(2-amino-2-methyl-propoxy)-phenylamino]-phenyl}-ethylamino)-1-hydroxy-ethyl]-8-hydroxy-1H-quinolin-2-one 4-methoxy cinnamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-[(R)-2-(2-{4-[4-(2-amino-2-methyl-propoxy)-phenylamino]-phenyl}-ethylamino)-1-hydroxy-ethyl]-8-hydroxy-1H-quinolin-2-one (0.101 g) was slurried in aqueous tetrahydrofuran (1:1 THF:H2O vol/vol, 1.2 mL). 4-Methoxycinnamic acid (0.036 g, predominantly trans) was added to the mixture. A solution formed before crystallisation spontaneously occurred. The resultant slurry was stirred overnight at room temperature and then filtered. The filtered solid was washed with aqueous tetrahydrofuran (1:1 THF:H2O vol/vol, 3×0.2 mL) and dried at 45° C. in vacuo overnight to give the title compound.

Workup

  1. customA solution formed before crystallisation
  2. filtrationfiltered
  3. washThe filtered solid was washed with aqueous tetrahydrofuran (1:1 THF:H2O vol/vol, 3×0.2 mL)
  4. customdried at 45° C. in vacuo overnight

Sources & evidence

ORD record
ord-e8dbd62057324b3c87e87afe5b7a6efc
Source dataset
uspto-grants-2010_08
Patent number
US07772250B2

Reaction notes

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