Triethylamine → HCID 67007260, compound

HRID 1187754Notes

Reaction equation

HRID 1187754 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[N:16]=[C:15]([N:17]3[CH2:20][CH:19]([OH:21])[CH2:18]3)[CH:14]=[C:13]([NH:22][C:23]3[CH:28]=[N:27][CH:26]=[CH:25][N:24]=3)[N:12]=2)[CH3:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl-].[NH4+]>CS(C)=O.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[N:16]=[C:15]([N:17]3[CH2:20][C:19](=[O:21])[CH2:18]3)[CH:14]=[C:13]([NH:22][C:23]3[CH:28]=[N:27][CH:26]=[CH:25][N:24]=3)[N:12]=2)[CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 46865138HCID 46865138, compound

Product 1

HCID 67007260HCID 67007260, compoundYield 32.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
15 °C

Procedure

156 mg of (S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}azetidin-3-ol (Example 72) was dissolved in 1 ml of dimethyl sulfoxide, and 571 μl of triethylamine was added thereto and cooled to 15° C. 0.5 ml of dimethyl sulfoxide suspension including 388 mg of pyridine-trisulfur oxide complex was added thereto, and the mixture was stirred at room temperature overnight. Ice and saturated ammonium chloride aqueous solution were added to the reaction solution, and the mixture was stirred for 15 minutes, and diluted with ethyl acetate, and the organic layer was washed with saturated ammonium chloride aqueous solution and water in turn, and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 50 mg of the objective compound as a brown amorphous solid.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 15 minutes
  3. washthe organic layer was washed with saturated ammonium chloride aqueous solution and water in turn
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-11083583b65d44c38b4324ac269db4f7
Source dataset
uspto-grants-2014_03
Patent number
US08673891B2

Reaction notes

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