Benzylamine → HCID 178522804, compound

HRID 45827Notes

Reaction equation

HRID 45827 reaction equation
Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.Cl.[N:33]1[CH:38]=[CH:37][C:36]([C:39]2[C:40]([C:44]3[CH:45]=[C:46]([CH:50]=[CH:51][CH:52]=3)[C:47]([OH:49])=O)=[N:41][NH:42][CH:43]=2)=[CH:35][CH:34]=1.[CH2:53]([NH2:60])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>C(Cl)Cl.CN(C=O)C.O>[CH2:53]([NH:60][C:47](=[O:49])[C:46]1[CH:50]=[CH:51][CH:52]=[C:44]([C:40]2[C:39]([C:36]3[CH:35]=[CH:34][N:33]=[CH:38][CH:37]=3)=[CH:43][NH:42][N:41]=2)[CH:45]=1)[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

9

Reactant 5

HCID 7504BenzylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178479744HCID 178479744, compound

Product 1

HCID 178522804HCID 178522804, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (0.029 g, 0.15 mmol, 1.5 eq) in dry DCM (1 mL) and a solution of 1-hydroxybenzotriazole (0.020 g, 0.15 mmol, 1.5 eq) and DIPEA (0.064 g, 0.50 mmol, 5 eq) in dry DMF (0.1 mL) were added to 3-(4-pyridin-4-yl-1H-pyrazol-3-yl)-benzoic acid hydrochloride (0.030 g, 0.10 mmol, 1 eq) in dry DMF (0.200 ml). Benzylamine (2 eq) was added to the reaction mixture, which was stirred at room temperature for 24 h. Distilled water (1.5 mL) was poured into the suspension that was stirred for 1 h at room temperature and the organic layer was separated by filtration through Alltech Separator Tube. The solvent was evaporated and reverse phase purification of the crude afforded the final product as a solid.

Workup

  1. stirringwas stirred for 1 h at room temperature
  2. customthe organic layer was separated by filtration through Alltech Separator Tube
  3. customThe solvent was evaporated
  4. customreverse phase purification of the crude

Sources & evidence

ORD record
ord-60ee773cb3c343d9adaea892fcf465d5
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

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