Hydroxyamine hydrochloride → HCID 136146831, compound

HRID 1674400Notes

Reaction equation

HRID 1674400 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]3[C:17](=[O:18])[N:16]([CH2:19][C:20]4[CH:25]=[CH:24][C:23]([C:26]5[C:27]([C:32]#[N:33])=[CH:28][CH:29]=[CH:30][CH:31]=5)=[CH:22][CH:21]=4)[C:15]([CH2:34][CH2:35][CH3:36])=[N:14][C:13]=3[CH3:37])=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.Cl.[NH2:39]O.[C:41](=[O:44])([O-])[OH:42].[Na+]>CS(C)=O.C(OCC)(=O)C>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]([C:12]3[C:17](=[O:18])[N:16]([CH2:19][C:20]4[CH:25]=[CH:24][C:23]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=5[C:32]5[NH:39][C:41](=[O:44])[O:42][N:33]=5)=[CH:22][CH:21]=4)[C:15]([CH2:34][CH2:35][CH3:36])=[N:14][C:13]=3[CH3:37])=[CH:10][CH:11]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 59469468HCID 59469468, compound

Product 1

HCID 136146831HCID 136146831, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

4′-{[5-[4-(Cyclopropylmethoxy)phenyl]-4-methyl-6-oxo-2-propylpyrimidin-1(6H)-yl]methyl}biphenyl-2-carbonitrile (0.56 g) was dissolved in dimethyl sulfoxide (5 mL), and hydroxylamine hydrochloride (0.79 g) and sodium hydrogen carbonate (1.2 g) were added. The mixture was stirred overnight at 90° C. After cooling, the reaction mixture was diluted with ethyl acetate, washed with water, dried over sodium sulfate and concentrated. The residue was dissolved in tetrahydrofuran (5 mL), and N,N′-carbonyldiimidazole (0.28 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.26 mL) were added. After stirring for 30 min, the reaction mixture was diluted with ethyl acetate, washed with 1 M hydrochloric acid, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.49 g, 78%).

Workup

  1. temperatureAfter cooling
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in tetrahydrofuran (5 mL)
  6. additionN,N′-carbonyldiimidazole (0.28 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.26 mL) were added
  7. stirringAfter stirring for 30 min
  8. additionthe reaction mixture was diluted with ethyl acetate
  9. washwashed with 1 M hydrochloric acid
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated
  12. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e7433e619a0742108f4871581e27faf9
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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