Cesium carbonate → HCID 178431654, compound

HRID 339838Notes

Reaction equation

HRID 339838 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([CH3:15])([CH3:14])[O:12][C:11]([NH:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[N:10][S:9]2(=[O:24])=[O:23])[CH:5]=[CH:6][CH:7]=1.[N:25]1[CH:30]=[C:29](B(O)O)[CH:28]=[N:27][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O>[CH:17]1([NH:16][C:11]2[O:12][C:13]([CH3:15])([CH3:14])[CH:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([C:29]4[CH:30]=[N:25][CH:26]=[N:27][CH:28]=4)[CH:3]=3)[S:9](=[O:24])(=[O:23])[N:10]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 1784316525-(3-bromophenyl)-N-cyclohexyl-6,6-dimethyl-4,4-dioxo-5H-1,4,3-oxathiazin-2-amine

Product 1

HCID 178431654HCID 178431654, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Under inert gas, 80 mg of [5-(3-bromophenyl)-6,6-dimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda6-1,4,3-oxathiazin-2-yl]cyclohexylamine, 30 mg of pyrimidine-5-boronic acid and 251 mg of cesium carbonate were dissolved in a mixture of 1.2 ml of dioxane and 0.4 ml of water. After purging with argon for 10 minutes, 15 mg of dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium were added and the reaction mixture was stirred at 80° C. for 2 hours. After cooling to room temperature, the mixture was admixed with 50 ml of ethyl acetate and washed with 15 ml of water and 15 ml of saturated aqueous sodium chloride solution, and the organic phase was dried over MgSO4 and concentrated by rotary evaporation. The residue was purified in a purification laboratory by means of preparative HPLC. The product-containing fractions were combined and lyophilized. This gave the product (6.4 mg) with a molecular weight of 414.5 g/mol (C21H26N4O3S); MS (ESI): m/e=415 (M+H+).

Workup

  1. customAfter purging with argon for 10 minutes
  2. addition15 mg of dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium were added
  3. temperatureAfter cooling to room temperature
  4. washwashed with 15 ml of water and 15 ml of saturated aqueous sodium chloride solution
  5. dry with materialthe organic phase was dried over MgSO4
  6. concentrationconcentrated by rotary evaporation
  7. customThe residue was purified in a purification laboratory by means of preparative HPLC

Sources & evidence

ORD record
ord-7d86a6b6e67c48f8ab1eb9f957198ed6
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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