Water → Batefenterol Succinate

HRID 2423014Notes

Reaction equation

HRID 2423014 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].O>C(O)C>[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

5

Reactant 3

HCID 962WaterHCID 1110Succinic AcidHCID 10372836Batefenterol

Product 1

HCID 16718568Batefenterol SuccinateYield 41.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
70 °C

Procedure

Ethanol (14 ml) was added to 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 (1.5 g) and heated at ˜70° C. for 1 h. The temperature was then lowered to 50° C. and succinic acid (251.25 mg, 1.05 equiv) in ethanol (2 ml) was added portionwise over approximately 4 hours. After all the acid was added, water (2.25 ml) was added, followed by a further 30 min at 50° C. The reaction was then temperature cycled between 0° C. and 40° C. over 3 days. The resulting white solid was isolated by filtration, washed with ethanol and dried in a vacuum oven at ambient temperature, to provide the title compound as a crystalline solid (727 mg).

Workup

  1. customwas then lowered to 50° C.
  2. additionAfter all the acid was added
  3. waittemperature cycled between 0° C. and 40° C. over 3 days
  4. customThe resulting white solid was isolated by filtration
  5. washwashed with ethanol
  6. customdried in a vacuum oven at ambient temperature

Sources & evidence

ORD record
ord-193ddf90a01945a4b5d5b3268937dd7c
Source dataset
uspto-grants-2011_06
Patent number
US07960551B2

Reaction notes

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