Cyclohexanecarboxaldehyde → HCID 24897730, compound

HRID 1913191Notes

Reaction equation

HRID 1913191 reaction equation
[CH:1]1([CH:7]=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.Cl.[NH2:11][CH2:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([N:19]2[C:23](=[O:24])[C:22]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)=[CH:21][NH:20]2)[CH:14]=1.C(N(C(C)C)CC)(C)C.[BH4-].[Na+]>C(O)C.O>[CH:1]1([CH2:7][NH:11][CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[C:15]([N:19]3[C:23](=[O:24])[C:22]([C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)=[CH:21][NH:20]3)[CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 16275CyclohexanecarboxaldehydeHCID 81531DiisopropylethylamineHCID 4311764Sodium borohydrideHCID 68704213HCID 68704213, compound

Product 1

HCID 24897730HCID 24897730, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

11.2 mg (100 μmol) of cyclohexanecarbaldehyde are initially charged, 34.0 mg (100 mol) of the compound from Example 4A, dissolved in 0.6 ml of ethanol, and 25.8 mg (200 μmol) of diisopropylethylamine are added and the mixture is stirred at RT overnight. 5.7 mg (150 μmol) of sodium borohydride are then added, and the mixture is shaken at RT for 3 h. 100 μl of water are then added, and the mixture is concentrated. The residue is taken up in DMSO, the precipitate is filtered off and the filtrate is purified by preparative HPLC (Method 4).

Workup

  1. stirringthe mixture is shaken at RT for 3 h
  2. concentrationthe mixture is concentrated
  3. filtrationthe precipitate is filtered off
  4. customthe filtrate is purified by preparative HPLC (Method 4)

Sources & evidence

ORD record
ord-27ec9d9cee0349718bc78a75903dbea3
Source dataset
uspto-grants-2013_12
Patent number
US08609698B2

Reaction notes

Loading…