Potassium Sodium Tartrate → HCID 86707769, compound

HRID 2410115Notes

Reaction equation

HRID 2410115 reaction equation
C[Al](C)C.[Cl:5][C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][C:12]=1[F:13])[NH2:9].C([O:16][C:17]([C:19]1[N:20]=[C:21]([Br:37])[N:22]([CH:33]2[CH2:36][CH2:35][CH2:34]2)[C:23]=1[CH:24]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)[OH:25])=O)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.O>[Cl:5][C:6]1[CH:7]=[C:8]([NH:9][C:17]([C:19]2[N:20]=[C:21]([Br:37])[N:22]([CH:33]3[CH2:34][CH2:35][CH2:36]3)[C:23]=2[CH:24]([C:26]2[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=2)[OH:25])=[O:16])[CH:10]=[CH:11][C:12]=1[F:13]

Participants

7

Reactant 4

HCID 9357Potassium Sodium TartrateHCID 97083-Chloro-4-fluoroanilineHCID 16682925TrimethylaluminumHCID 86707770HCID 86707770, compound

Product 1

HCID 86707769HCID 86707769, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

To the stirred solution of trimethylaluminium (2M in toluene) (0.87 ml, 1.74 mmol) was added drop wise the solution of 3-chloro-4-fluoroaniline (0.267 g, 1.80 mmol) and toluene (2.0 ml) at 0° C. and then the temperature was raised to rt. The mixture was concentrated. 2-bromo-5[(4-chloro-phenyl)-hydroxyl-methyl]-1-cyclobutyl-1H-imidazole-4-carboxylic acid ethyl ester (step AK2; 0.502 g, 1.20 mol) in toluene (6.0 ml) was added and the mixture was stirred for 3 h at 80° C., then cooled to rt. The reaction mixture was taken up in Teac (40 ml), poured onto “Rochelle Salt-Solution” (1M in water) and stirred for 15 min at rt. The organic phase was washed with brine and dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (EtOAc/hexane, 1:4), then triturated in hexane to afford the title compound. tR: 1.46 min (LC-MS 2); ESI-MS: 514.1 [M+H]+ (LC-MS 2).

Workup

  1. concentrationThe mixture was concentrated
  2. temperaturecooled to rt
  3. stirringstirred for 15 min at rt
  4. washThe organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (EtOAc/hexane, 1:4)
  9. customtriturated in hexane

Sources & evidence

ORD record
ord-58ead3099e9941ffa2f331f8d3b5360c
Source dataset
uspto-grants-2014_08
Patent number
US08815926B2

Reaction notes

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