Pyridine → HCID 72575771, compound

HRID 1365922Notes

Reaction equation

HRID 1365922 reaction equation
ClC(Cl)(OC(=O)[O:6][C:7]([Cl:10])(Cl)Cl)Cl.[Cl:13][C:14]1[CH:15]=[C:16]([C:21]([CH3:39])([CH3:38])[C:22]([N:24]([C@H:26]2[C@H:30]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[CH2:29][NH:28][CH2:27]2)[CH3:25])=[O:23])[CH:17]=[C:18]([Cl:20])[CH:19]=1.N1C=CC=CC=1>C(Cl)Cl>[Cl:13][C:14]1[CH:15]=[C:16]([C:21]([CH3:39])([CH3:38])[C:22]([N:24]([CH3:25])[CH:26]2[CH:30]([C:31]3[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=3)[CH2:29][N:28]([C:7]([Cl:10])=[O:6])[CH2:27]2)=[O:23])[CH:17]=[C:18]([Cl:20])[CH:19]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 59840087HCID 59840087, compound

Product 1

HCID 72575771HCID 72575771, compoundYield 196.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of carbonic acid ditrichloromethyl ester (triphosgene) (12 mg, 0.040 mmol) in CH2Cl2 (3 ml) at −78° C., was added a solution of rac-2-(3,5-dichloro-phenyl)-N-[(3S,4R)-4-(4-fluoro-phenyl)-pyrrolidin-3-yl]-N-methyl-isobutyramide (Intermediate VII-5), (41 mg, 0.10 mmol) and pyridine (0.02 ml, 0.22 mmol) in CH2Cl2 (2 ml) over 30 minutes. The temperature was raised to RT, and stirring was continued for 2 hours. The organic phase was washed with H2O, dried over Na2SO4. Purification by flash chromatography (SiO2, EtOAc/Hx 1:1) yielded 37 mg (79%) of the title compound as_colorless oil.

Workup

  1. washThe organic phase was washed with H2O
  2. dry with materialdried over Na2SO4
  3. customPurification by flash chromatography (SiO2, EtOAc/Hx 1:1)

Sources & evidence

ORD record
ord-6286246df85648df84d6d788ed111588
Source dataset
uspto-grants-2011_02
Patent number
US07893062B2

Reaction notes

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