HCID 178418361, compound → HCID 178464362, compound

HRID 1399518Notes

Reaction equation

HRID 1399518 reaction equation
C([O:8][C:9](=[O:62])[CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][N:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=2[CH2:31][N:32]([C@H:46]([C:48]2[CH:53]=[C:52]([C:54]([F:57])([F:56])[F:55])[CH:51]=[C:50]([C:58]([F:61])([F:60])[F:59])[CH:49]=2)[CH3:47])[C:33]2[N:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][S:42]([CH3:45])(=[O:44])=[O:43])=[CH:35][N:34]=2)[CH2:19][CH3:20])[CH2:13][CH2:12]1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[F:61][C:58]([F:59])([F:60])[C:50]1[CH:49]=[C:48]([CH:46]([N:32]([CH2:31][C:22]2[CH:23]=[C:24]([C:27]([F:30])([F:28])[F:29])[CH:25]=[CH:26][C:21]=2[N:18]([CH2:17][C@H:14]2[CH2:15][CH2:16][C@H:11]([CH2:10][C:9]([OH:62])=[O:8])[CH2:12][CH2:13]2)[CH2:19][CH3:20])[C:33]2[N:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][S:42]([CH3:45])(=[O:43])=[O:44])=[CH:35][N:34]=2)[CH3:47])[CH:53]=[C:52]([C:54]([F:57])([F:56])[F:55])[CH:51]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178464367HCID 178464367, compound

Product 1

HCID 178464362HCID 178464362, compoundYield 103.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Under nitrogen atmosphere, a solution of (S)-trans-{4-[({2-[({1-[3,5-bis(trifluoromethyl)phenyl]ethyl}{5-[2-(methylsulfonyl)ethoxy]pyrimidin-2-yl}amino)methyl]-4-(trifluoromethyl)phenyl}(ethyl)amino)methyl]cyclohexyl}acetic acid benzyl ester (7) (34.2 g, 37.88 mmol, >99% ee) obtained in Step 5 in ethanol (340 mL) was added with 10% Pd—C (wet, 3.4 for hydrogen substitution, and then the mixture was stirred at room temperature for 2 hours. The reaction suspension was filtered through Celite, and washed with ethanol (50 mL), and the washing solution was concentrated under reduced pressure to obtain substantially optically pure trans-{4-[({2-[({1-[3,5-bis(trifluoromethyl)phenyl]ethyl}{5-[2-(methylsulfonyl)ethoxy]pyrimidin-2-yl}amino)methyl]-4-(trifluoromethyl)phenyl}(ethyl)amino)methyl]cyclohexyl}acetic acid (III) (white amorphous, 31.78 g, yield: 100%).

Workup

  1. filtrationThe reaction suspension was filtered through Celite
  2. washwashed with ethanol (50 mL)
  3. concentrationthe washing solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7fab76e39a0d41f7a2cf6cfe1a0581a4
Source dataset
uspto-grants-2014_12
Patent number
US08906895B2

Reaction notes

Loading…