Cyclamen aldehyde → HCID 66577251, compound

HRID 1528728Notes

Reaction equation

HRID 1528728 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[NH2:14])=[CH:4][CH:3]=1.[CH:15]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([CH3:28])[CH:26]=O)=[CH:20][CH:19]=1)([CH3:17])[CH3:16].C([BH3-])#N.[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[NH:14][CH2:26][CH:25]([CH3:28])[CH2:24][C:21]2[CH:20]=[CH:19][C:18]([CH:15]([CH3:17])[CH3:16])=[CH:23][CH:22]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 517827Cyclamen aldehydeHCID 5003444Sodium cyanoborohydrideHCID 582185375-(4-Bromophenyl)-3-methylisoxazol-4-amine

Product 1

HCID 66577251HCID 66577251, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-ylamine (0.300 g, 1.19 mmol) and 3-(4-isopropylphenyl)isobutyraldehyde (0.272 g, 1.43 mmol) were combined in toluene (3 mL) and stirred at 110° C. for 1 hour. After cooling to room temperature, toluene was removed under vacuum and the mixture was diluted with THF (4 mL). Sodium cyanoborohydride (0.188 g, 2.98 mmol) was added, and the reaction was stirred at room temperature for 1 hour. The mixture was adsorbed onto silica gel and purified by silica gel chromatography to give the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. customtoluene was removed under vacuum
  3. additionthe mixture was diluted with THF (4 mL)
  4. stirringthe reaction was stirred at room temperature for 1 hour
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-024ca7e4f1dd43ae9836b3d8f2e5ee66
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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