Cesium carbonate → HCID 57595389, compound

HRID 1786025Notes

Reaction equation

HRID 1786025 reaction equation
[C:1]([N:4]([C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]([C:17]2[CH:22]=[CH:21][C:20](OS(C(F)(F)F)(=O)=O)=[CH:19][CH:18]=2)=[O:16])[C@@H:7]([CH3:31])[CH2:6]1)(=[O:3])[CH3:2].[CH2:39]([O:41][C:42]([CH:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1)=[O:43])[CH3:40].C([O-])([O-])=O.[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C1OCCOCCOCCOCCOCCOC1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:39]([O:41][C:42]([CH:44]1[CH2:49][CH2:48][N:47]([C:20]2[CH:19]=[CH:18][C:17]([C:15]([N:8]3[C:9]4[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=4)[C@H:5]([N:4]([C:1](=[O:3])[CH3:2])[C:32]4[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=4)[CH2:6][C@@H:7]3[CH3:31])=[O:16])=[CH:22][CH:21]=2)[CH2:46][CH2:45]1)=[O:43])[CH3:40]

Participants

8

Reactant 5

HCID 10796Cesium carbonateHCID 2855718-Crown-6HCID 70770Ethyl 4-piperidinecarboxylateHCID 634876Binap, (A+-)-HCID 87625288HCID 87625288, compound

Product 1

HCID 57595389HCID 57595389, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

(2S,4R)-1-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-piperidine-4-carboxylic acid ethyl ester was prepared from (2S,4R)-trifluoro-methanesulfonic acid 4-{4-[acetyl(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl ester by adding piperidine-4-carboxylic acid ethyl ester (4 eq.), Cs2CO3 (3 eq.), 10% Pd2(dba)3, BINAP (0.20 equ), and 10% 18-Crown-6 (0.10 eq.) in toluene at 110° C. over night. The reaction mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and water, then extracted three times with ethyl acetate, dried over MgSO4, filtered and concentrated down. The crude residue was purified by HPLC to afford the product.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate and water
  3. extractionextracted three times with ethyl acetate
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated down
  7. customThe crude residue was purified by HPLC
  8. customto afford the product

Sources & evidence

ORD record
ord-4b58686b737a43c9820eb1d963663eba
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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