Dimethylformamide → HCID 9969734, compound

HRID 1057374Notes

Reaction equation

HRID 1057374 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[NH:9][C:8]2=[O:16])[CH2:3][CH2:2]1.[CH3:17][N:18]([CH:20]=O)[CH3:19].[C:22](#[N:24])C>C(OCC)(=O)C>[N:24]1[CH:22]=[C:17]([CH2:11][CH2:10][CH2:15][N:1]2[CH2:2][CH2:3][CH:4]([N:7]3[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[NH:9][C:8]3=[O:16])[CH2:5][CH2:6]2)[N:18]2[CH:20]=[CH:4][CH:3]=[CH:2][C:19]=12

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6342AcetonitrileHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one

Product 1

HCID 9969734HCID 9969734, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

240 mg (2.21 mmol) of 1-piperidin-4-yl-1,3-dihydrobenzimidazol-2-one is dissolved in 3.5 ml of acetonitrile and 3.5 ml of DMF at 50° C. and at this temperature a solution of 240 mg (1.00 mmol) of the compound of Example 11.3 in 7.5 ml of ethyl acetate is added dropwise. The mixture is initially stirred for 5 hours at 50° C., then for 72 hours at RT. The solution is evaporated down and the residue is purified by flash chromatography (dichloromethane/ethanol 90:10), yielding 48 mg of product. MS: m/z 376 [(M+H)+]; melting point: 185° C.

Workup

  1. waitfor 72 hours at RT
  2. customThe solution is evaporated down
  3. customthe residue is purified by flash chromatography (dichloromethane/ethanol 90:10)

Sources & evidence

ORD record
ord-b1037ab2c08148c99c5989bf4a691d6c
Source dataset
uspto-grants-2003_02
Patent number
US06514969B2

Reaction notes

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