Acetic Acid → 4-({[4-(9-Phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]amino}methyl)phenol

HRID 1678787Notes

Reaction equation

HRID 1678787 reaction equation
[C:1]1([C:7]2[C:8]([C:20]3[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=3)=[N:9][C:10]3[CH:11]=[CH:12][N:13]4[CH:19]=[N:18][N:17]=[C:14]4[C:15]=3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C=O)C>[C:1]1([C:7]2[C:8]([C:20]3[CH:21]=[CH:22][C:23]([CH2:24][NH:28][CH2:29][C:30]4[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=4)=[CH:26][CH:27]=3)=[N:9][C:10]3[CH:11]=[CH:12][N:13]4[CH:19]=[N:18][N:17]=[C:14]4[C:15]=3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 974724-HydroxybenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 594729044-(9-Phenyl[1,2,4]triazolo[3,4-f][1,6]naphthyridin-8-yl)benzaldehyde

Product 1

HCID 159796384-({[4-(9-Phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]amino}methyl)phenol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-2 (0.05 g, 0.14 mMol) and 4-(aminomethyl)phenol (0.04, 0.35 mMol) in DMF (0.5 mL) was added acetic acid (0.04 mL, 0.7 mMol). After stirring for 2 hours at room temperature, sodium triacetoxyborohydride (0.06 g, 0.3 mMol) was added. After stirring overnight, the reaction was filtered through a syringe filter and purified on a C18 reverse phase HPLC to yield 19-1 as a solid. LC/MS (M+1) calculated: 458.5; observed: 458.3.

Workup

  1. stirringAfter stirring overnight
  2. filtrationthe reaction was filtered through a syringe
  3. filtrationfilter
  4. custompurified on a C18 reverse phase HPLC

Sources & evidence

ORD record
ord-cb1b955219924c3894f8957ff0d5a6c4
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

Loading…