Potassium Carbonate → HCID 89586269, compound

HRID 574260Notes

Reaction equation

HRID 574260 reaction equation
[C:1]([O:5][C:6](=[O:54])[NH:7][C@H:8]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=1[OH:53])[CH2:9][N:10]1[C:15](=[O:16])[C:14]([N:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]3[O:25][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:27][CH:28]=3)[CH2:19][CH2:18]2)=[C:13]([CH3:33])[N:12]([CH2:34][C:35]2[C:40]([C:41]([F:44])([F:43])[F:42])=[CH:39][CH:38]=[CH:37][C:36]=2[F:45])[C:11]1=[O:46])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:61]([O:65][C:66](=[O:69])[CH2:67]Br)([CH3:64])([CH3:63])[CH3:62]>CN(C=O)C.ClCCl>[C:61]([O:65][C:66](=[O:69])[CH2:67][O:53][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=1[C@@H:8]([NH:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:54])[CH2:9][N:10]1[C:15](=[O:16])[C:14]([N:17]2[CH2:18][CH2:19][N:20]([CH2:23][C:24]3[O:25][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:27][CH:28]=3)[CH2:21][CH2:22]2)=[C:13]([CH3:33])[N:12]([CH2:34][C:35]2[C:40]([C:41]([F:43])([F:44])[F:42])=[CH:39][CH:38]=[CH:37][C:36]=2[F:45])[C:11]1=[O:46])([CH3:64])([CH3:63])[CH3:62]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 87285764HCID 87285764, compound

Product 1

HCID 89586269HCID 89586269, compoundYield 44.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of [(R)-2-{3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-5-[4-(5-trifluoromethyl-furan-2-ylmethyl)-piperazin-1-yl]-3,6-dihydro-2H-pyrimidin-1-yl}-1-(2-hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester (100 mg, 0.13 mmol), potassium carbonate (36 mg, 0.26 mmol), and bromo-acetic acid tert-butyl ester (38 μl, 0.26 mmol) were dissolved at 70° C. for 4 hrs in DMF (1 mL) with stirring, and then chilled to room temperature. The solution was diluted in dichloromethane and washed with an aqueous saturated sodium bicarbonate solution. The organic layer thus formed was separated and concentrated, and the residue was purified using silica gel chromatography (eluent: hexane/ethyl acetate, 2/1) and dried in a vacuum to afford 51 mg of the compound as a white oil (yield 44%).

Workup

  1. washwashed with an aqueous saturated sodium bicarbonate solution
  2. customThe organic layer thus formed
  3. customwas separated
  4. concentrationconcentrated
  5. customthe residue was purified
  6. customdried in a vacuum

Sources & evidence

ORD record
ord-a332d1dd6eb2439d913f7e42d47c4c98
Source dataset
uspto-grants-2015_05
Patent number
US09034850B2

Reaction notes

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