Benzylamine → HCID 69433038, compound

HRID 1269720Notes

Reaction equation

HRID 1269720 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:10][CH2:11][C:12]([NH:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][N:19]=[CH:18]2)=[O:13].CCCCCC>CN(C)C=O>[CH2:1]([NH:8][CH2:10][CH2:11][C:12]([NH:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][N:19]=[CH:18]2)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 8058HexaneHCID 17164503Propanamide, 3-chloro-N-1H-indazol-5-yl-

Product 1

HCID 69433038HCID 69433038, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

N-benzylamine (4.0 ml, 36.5 mmol) was added to a solution of 3-chloro-N-(1H-indazol-5-yl)propanamide (1.70 g, 7.60 mmol) in N,N-dimethylformamide (2 ml), and the resulting mixture was stirred at 80° C. for 1 hour. Then, the reaction solution was cooled to 0° C. and hexane was added thereto to effect suspension. The solid precipitated was collected by filtration and purified by a silica gel column chromatography (eluent: chloroform/methanol=20/1) to obtain N3-benzyl-N1-(1H-indazol-5-yl)-β-alaninamide (1.00 g, 45%).

Workup

  1. temperatureThen, the reaction solution was cooled to 0° C.
  2. customThe solid precipitated
  3. filtrationwas collected by filtration
  4. custompurified by a silica gel column chromatography (eluent: chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-670ffa715ce042d595c415330152d993
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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