5-Chloro-salicylaldehyde → HCID 178488388, compound

HRID 530419Notes

Reaction equation

HRID 530419 reaction equation
[Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=O)[C:5]([OH:10])=[CH:4][CH:3]=1.C([BH3-])#N.[Na+].[NH:15]=[C:16]1[N:20]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[C:19](=[O:27])[C:18]([C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=2)([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[NH:17]1>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH2:7][N:24]1[CH2:25][CH2:26][CH:21]([N:20]2[C:19](=[O:27])[C:18]([C:36]3[CH:37]=[CH:38][C:39]([O:42][CH3:43])=[CH:40][CH:41]=3)([C:28]3[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=3)[NH:17][C:16]2=[NH:15])[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 124815-Chloro-salicylaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178488387HCID 178488387, compound

Product 1

HCID 178488388HCID 178488388, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Chlorosalicylaldehyde (0.24 g, 1.53 mmol), sodium cyanoborohydride (0.33 g, 5.25 mmol) and 2-imino-5,5-bis(4-methoxyphenyl)-3-(piperidin-4-yl)imidazolidin-4-one (0.41 g, 1.04 mmol) were dissolved in ethanol and the solution was stirred at room temperature overnight. The mixture was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. The residue was purified over a silica column (MeOH/DCM=1/20) to give the title compound as a white solid (0.18 g, 33% yield).

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified over a silica column (MeOH/DCM=1/20)

Sources & evidence

ORD record
ord-cb9e228a9d0347dbb0c3dc52f33067ca
Source dataset
uspto-grants-2016_05
Patent number
US09353089B2

Reaction notes

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