Batefenterol → Batefenterol edisylate

HRID 2112279Notes

Reaction equation

HRID 2112279 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][NH:9][CH2:10][C@H:11]([OH:24])[C:12]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]3[C:13]=2[CH:14]=[CH:15][C:16](=[O:23])[NH:17]3)[C:5]([O:25][CH3:26])=[CH:4][C:3]=1[NH:27][C:28]([CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][CH:35]([O:38][C:39](=[O:53])[NH:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH2:34][CH2:33]1)=[O:29].O.O.[CH2:56]([S:62]([OH:65])(=[O:64])=[O:63])[CH2:57][S:58]([OH:61])(=[O:60])=[O:59]>C(O)(C)C.O>[CH2:56]([S:62]([OH:65])(=[O:64])=[O:63])[CH2:57][S:58]([OH:61])(=[O:60])=[O:59].[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][NH:9][CH2:10][C@H:11]([OH:24])[C:12]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]3[C:13]=2[CH:14]=[CH:15][C:16](=[O:23])[NH:17]3)[C:5]([O:25][CH3:26])=[CH:4][C:3]=1[NH:27][C:28]([CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][CH:35]([O:38][C:39](=[O:53])[NH:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH2:34][CH2:33]1)=[O:29]

Participants

5

Reactant 2

HCID 10372836BatefenterolHCID 57346009Ethane-1,2-disulfonic acid--water (1/2)

Product 1

HCID 11629376Batefenterol edisylateYield 95.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

Biphenyl-2-ylcarbamic acid 1-[2-(2-chloro-4-{[(r)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]methyl}-5-methoxyphenylcarbamoyl)-ethyl]piperidin-4-yl ester (5 g, 6.75 mmol, >99% pure) was dissolved in isopropanol (100 mL), followed by addition of ethane disulfonic acid dihydrate (1.525 mg, 6.75 mmol) dissolved in water (20 mL). The resulting slurry was stirred at room temperature for 1 hour, and then at ˜30° C. overnight. The title compound (6.0 g) was isolated as a white powder. The product was heated in 20% water in isopropanol (100 mL) at 30° C. for 48 hours. After cooling to room temperature, the resulting precipitate was isolated by filtration and dried in air for 2 hours to yield the title compound (5.4 g).

Workup

  1. customat ˜30° C.
  2. customovernight

Sources & evidence

ORD record
ord-edc39e83adc1453c991b72e2d296c34f
Source dataset
uspto-grants-2009_04
Patent number
US07521558B2

Reaction notes

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