3-Carboxybenzaldehyde → HCID 9980457, compound

HRID 2111969Notes

Reaction equation

HRID 2111969 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][NH:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)=[O:8].[C:24]([C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH:30]=O)([OH:26])=[O:25].[BH4-].[Na+]>C(O)(=O)C>[C:12]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:14][C:9]([C:7]([NH:6][CH2:5][C:4]2[CH:3]=[C:2]([NH:1][CH2:30][C:29]3[CH:28]=[C:27]([CH:34]=[CH:33][CH:32]=3)[C:24]([OH:26])=[O:25])[CH:23]=[CH:22][CH:21]=2)=[O:8])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 120773-CarboxybenzaldehydeHCID 4311764Sodium borohydrideHCID 68869657HCID 68869657, compound

Product 1

HCID 9980457HCID 9980457, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-(3-aminobenzyl)-1,1′-biphenyl-4-carboxamide (20 mg, 0.07 mmol) was dissolved in acetic acid (0.5 ml). 3-Carboxybenzaldehyde (14 mg, 0.09 mmol) was added and then sodium borohydride (11 mg, 0.28 mmol) was added. The mixture was stirred at room temperature for 2 hours and evaporated to dryness. DCM was added into the residue. The mixture was loaded on a column (ISOLUTE® SI, 500 mg/3 ml). It was eluted with DCM, MeOH/DCM (0.5:99.5) and then MeOH/DCM (1:99). The product fractions were combined and the solvent was removed, Re-chromatography of the residue on a column (ISOLUTE® SI, 1 g/6 ml) using DCM, MeOH/DCM (0.5:99.5) and then MeOH/DCM (1:99) as eluant gave 9 mg the desired product, yield 31%.

Workup

  1. customevaporated to dryness
  2. additionDCM was added into the residue
  3. washIt was eluted with DCM, MeOH/DCM (0.5:99.5)
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-6c709838121041e289db0d495d180ef1
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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