Acetic Acid → HCID 67007458, compound

HRID 1187755Notes

Reaction equation

HRID 1187755 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][C:19](=O)[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.[CH3:29][NH:30][CH3:31].O1CCCC1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(OCC)(=O)C>[CH3:29][N:30]([CH3:31])[CH:19]1[CH2:20][N:17]([C:15]2[N:16]=[C:11]([NH:10][C@H:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH3:9])[N:12]=[C:13]([NH:22][C:23]3[CH:28]=[N:27][CH:26]=[CH:25][N:24]=3)[CH:14]=2)[CH2:18]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 22320367Dimethylamine tetrahydrofuranHCID 67007260HCID 67007260, compound

Product 1

HCID 67007458HCID 67007458, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

300 mg of (S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}azetidin-3-one was dissolved in 5 ml of 1,2-dichloroethane, and 12 ml of 2M dimethylamine/tetrahydrofuran solution and 290 μl of acetic acid were added thereto, and the mixture was stirred at room temperature for 30 minutes. 340 mg of sodium triacetoxyborohydride was added thereto, and the mixture was stirred at room temperature overnight. The reaction solution was diluted with ethyl acetate. The solution was washed in turn with a saturated aqueous solution of sodium bicarbonate and brine, and then 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 187 mg of the objective compound as brown powder.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. washThe solution was washed in turn with a saturated aqueous solution of sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1024a91a874f4cc48cbbe19b68e032d5
Source dataset
uspto-grants-2014_03
Patent number
US08673891B2

Reaction notes

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