Succinic Acid → Batefenterol Succinate

HRID 2423016Notes

Reaction equation

HRID 2423016 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].[C:54]([OH:61])(=[O:60])[CH2:55][CH2:56][C:57]([OH:59])=[O:58]>CO>[C:54]([OH:61])(=[O:60])[CH2:55][CH2:56][C:57]([OH:59])=[O:58].[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

4

Reactant 2

HCID 1110Succinic AcidHCID 10372836Batefenterol

Product 1

HCID 16718568Batefenterol SuccinateYield 42.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

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 (2 g) was dissolved in methanol (16 ml) at ˜70° C., over a period of 1 h. After a further 1 h, succinic acid (335 mg) in methanol (4 ml) was added and this was left to temperature cycle between 0° C. and 40° C. over 2 days. The resulting solid was isolated by filtration, washed with methanol, dried on filter paper and then dried at 40° C. in a vacuum oven overnight, to provide the title compound as a crystalline solid (979 mg). This was confirmed by DSC to be Form 2.

Workup

  1. waitthis was left to temperature cycle between 0° C. and 40° C. over 2 days
  2. customThe resulting solid was isolated by filtration
  3. washwashed with methanol
  4. customdried
  5. filtrationon filter paper
  6. customdried at 40° C. in a vacuum oven overnight

Sources & evidence

ORD record
ord-b26186a32a24443388b4dddbc7050e67
Source dataset
uspto-grants-2011_06
Patent number
US07960551B2

Reaction notes

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