Pyridine → HCID 59840082, compound

HRID 1365921Notes

Reaction equation

HRID 1365921 reaction equation
ClC(Cl)(OC(=O)[O:6][C:7]([Cl:10])(Cl)Cl)Cl.[F:13][C:14]([F:45])([F:44])[C:15]1[CH:16]=[C:17]([C:25]([CH3:43])([CH3:42])[C:26]([N:28]([C@H:30]2[C@H:34]([C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=3)[CH2:33][NH:32][CH2:31]2)[CH3:29])=[O:27])[CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1.N1C=CC=CC=1>C(Cl)Cl>[F:45][C:14]([F:13])([F:44])[C:15]1[CH:16]=[C:17]([C:25]([CH3:42])([CH3:43])[C:26]([N:28]([CH3:29])[C@H:30]2[C@H:34]([C:35]3[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=3)[CH2:33][N:32]([C:7]([Cl:10])=[O:6])[CH2:31]2)=[O:27])[CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 59840130HCID 59840130, compound

Product 1

HCID 59840082HCID 59840082, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of carbonic acid ditrichloromethyl ester (triphosgene) (31 mg, 0.10 mmol) in CH2Cl2 (5 ml) at 0° C., was added a solution of rac-2-(3,5-bis-trifluoromethyl-phenyl)-N-[(3S,4R)-4-(4-fluoro-phenyl)-pyrrolidin-3-yl]-N-methyl-isobutyramide (Intermediate VII-4), (100 mg, 0.21 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 25 mg (22%) 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-6d0fb5d11ff148b7aa1cb6afc64303f9
Source dataset
uspto-grants-2011_02
Patent number
US07893062B2

Reaction notes

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