Diethyl Pyrocarbonate → HCID 53361738, compound

HRID 1023368Notes

Reaction equation

HRID 1023368 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:28]=[CH:29]/[C:30]([OH:32])=O)[CH:5]=[C:6]([CH3:27])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)=[CH:11][N:10]=1.FC(F)(F)C(O)=O.[N:40]1([CH2:46][C:47]2[CH:52]=[CH:51][C:50]([CH2:53][CH2:54][O:55][C:56]3[CH:63]=[CH:62][C:59]([C:60]#[N:61])=[CH:58][CH:57]=3)=[CH:49][CH:48]=2)[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1.CCOC(OC(OCC)=O)=O.CCN(CC)CC>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:28]=[CH:29]/[C:30]([N:43]2[CH2:42][CH2:41][N:40]([CH2:46][C:47]3[CH:48]=[CH:49][C:50]([CH2:53][CH2:54][O:55][C:56]4[CH:57]=[CH:58][C:59]([C:60]#[N:61])=[CH:62][CH:63]=4)=[CH:51][CH:52]=3)[CH2:45][CH2:44]2)=[O:32])[CH:5]=[C:6]([CH3:27])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]([F:25])([F:26])[F:24])=[CH:21][CH:22]=2)=[CH:11][N:10]=1

Participants

7

Reactant 4

HCID 3051Diethyl PyrocarbonateHCID 8471TriethylamineHCID 67327057HCID 67327057, compoundHCID 67328153HCID 67328153, compound

Product 1

HCID 53361738HCID 53361738, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (E)-3-{3-chloro-5-methyl-4-[(5-{[4-(trifluoromethyl)benzyl]-oxy}pyridin-2-yl)oxy]phenyl}prop-2-enoic acid (139 mg) and 4-{2-[4-(piperazin-1-ylmethyl)-phenyl]ethoxy}benzonitrile trifluoroacetate (131 mg) in DMF (6 mL) was added DEPC (0.073 mL) and Et3N (0.165 mL) at 0° C. After stirring at 0° C. for 1 hour, to the reaction mixture was added H2O, and extracted with AcOEt. The organic layer was washed with saturated aqueous NaCl, dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt) to give 4-{2-[4-({4-[(E)-3-{3-chloro-5-methyl-4-[(5-{[4-(trifluoromethyl)benzyl]oxy}pyridin-2-yl)oxy]phenyl}prop-2-enoyl]piperazin-1-yl}methyl)phenyl]ethoxy}benzonitrile as a pale yellow amorphous (195 mg).

Workup

  1. extractionextracted with AcOEt
  2. washThe organic layer was washed with saturated aqueous NaCl
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (AcOEt)

Sources & evidence

ORD record
ord-4be07b9779d742d69c09405ad6250982
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

Loading…