4-Chlorobenzylamine → HCID 178522944, compound

HRID 456682Notes

Reaction equation

HRID 456682 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]2[NH:14][CH:13]=[C:12]([C:15]([OH:17])=O)[CH:11]=2)=[N:2]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[Cl:40][C:41]1[CH:48]=[CH:47][C:44]([CH2:45][NH2:46])=[CH:43][CH:42]=1>CN(C=O)C>[Cl:40][C:41]1[CH:48]=[CH:47][C:44]([CH2:45][NH:46][C:15]([C:12]2[CH:11]=[C:10]([C:3]3[C:4]4[C:5](=[N:6][CH:7]=[CH:8][CH:9]=4)[NH:1][N:2]=3)[NH:14][CH:13]=2)=[O:17])=[CH:43][CH:42]=1

Participants

6

Reactant 4

HCID 660364-ChlorobenzylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178524798HCID 178524798, compound

Product 1

HCID 178522944HCID 178522944, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(1H-pyrazolo[3,4-b]pyridin-3-yl)-1H-pyrrole-3-carboxylic acid (50 mg, 0.22 mmol), HOBt (74 mg, 2.5 eq.). EDAC•HCl (105 mg, 2.5 eq.), 4-chlorobenzylamine (4 eq.) and TEA (0.5 mL) in DMF (1 mL) was heated at 40° C. overnight. The reaction was concentrated and the residue was purified on a silica gel column to give the titled compound as a white solid.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-c61c9adccdd44b6980051043a77eee25
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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