Potassium Phosphate, Tribasic → HCID 178485321, compound

HRID 215959Notes

Reaction equation

HRID 215959 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:10]1[CH:11]=[C:12]([Cl:34])[C:13]([N:16]2[CH2:33][CH2:32][C:19]3([C:23](=[O:24])[N:22]([C@H:25]4[CH2:30][CH2:29][C@@H:28]([OH:31])[CH2:27][CH2:26]4)[CH2:21][CH2:20]3)[CH2:18][CH2:17]2)=[N:14][CH:15]=1.[CH3:35][NH:36][C:37]([C:39]1[CH:40]=[C:41](B(O)O)[CH:42]=[CH:43][CH:44]=1)=[O:38]>O.O1CCOCC1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:34][C:12]1[CH:11]=[C:10]([C:43]2[CH:44]=[C:39]([CH:40]=[CH:41][CH:42]=2)[C:37]([NH:36][CH3:35])=[O:38])[CH:15]=[N:14][C:13]=1[N:16]1[CH2:33][CH2:32][C:19]2([C:23](=[O:24])[N:22]([C@H:25]3[CH2:30][CH2:29][C@@H:28]([OH:31])[CH2:27][CH2:26]3)[CH2:21][CH2:20]2)[CH2:18][CH2:17]1

Participants

8

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27735243-(Methylcarbamoyl)benzeneboronic acidHCID 178517866HCID 178517866, compound

Product 1

HCID 178485321HCID 178485321, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

Potassium phosphate (0.017 g, 0.078 mmol) in water (0.10 mL) was added to a mixture of 8-(5-bromo-3-chloropyridin-2-yl)-2-(cis-4-hydroxycyclohexyl)-2,8-diazaspiro[4.5]decan-1-one (11.6 mg, 0.0262 mmol), 3-[(methylamino)carbonyl]phenylboronic acid (7.0 mg, 0.039 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.9 mg, 0.0008 mmol) in 1,4-dioxane (0.78 mL). The resulting mixture was heated and stirred at 120° C. for 2 h. The mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was dried over Na2SO4, filtered, concentrated under reduced pressure. The residue was purified by Prep-HPLC to afford the desired product. LCMS: (M+H)+=497.1/499.1.

Workup

  1. temperatureThe resulting mixture was heated
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by Prep-HPLC

Sources & evidence

ORD record
ord-0dfb7d2b0140422aa91cae6cd938a18b
Source dataset
uspto-grants-2012_06
Patent number
US08193207B2

Reaction notes

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