4-Methylmorpholine → HCID 11316822, compound

HRID 2186888Notes

Reaction equation

HRID 2186888 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][C:19]([NH:21][CH3:22])=[CH:20][C:13]=3[N:12]=2)=[CH:5][CH:4]=1)#[N:2].[C:23]([C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][C:33]([OH:35])=O)=[CH:27][CH:26]=1)#[N:24].CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C)C=O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][C:19]([N:21]([CH3:22])[C:33](=[O:35])[CH2:32][CH2:31][C:28]4[CH:27]=[CH:26][C:25]([C:23]#[N:24])=[CH:30][CH:29]=4)=[CH:20][C:13]=3[N:12]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 93617423-(4-Cyanophenyl)-propionic acidHCID 18763063HCID 18763063, compound

Product 1

HCID 11316822HCID 11316822, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[2-(4-cyanophenyl)-ethyl]-1-methyl-5-methylamino-benzimidazole (0.9 g, 3.1 mmol), 3-(p-cyanophenyl)-propionic acid (0.6 g, 3,4 mmol) and 0.5 mL of N-methylmorpholine are taken up in 10 mL of dimethylformamide. TBTU (1.2 g, 3.7 mmol) is added and the mixture is stirred for 16 h at ambient temperature. After dilution with 75 mL of ethyl acetate the mixture is washed with dilute aqueous NaOH or saturated NaHCO3 solution and with water, dried and evaporated down. The product is crystallised from ethyl acetate/diethylether.

Workup

  1. washAfter dilution with 75 mL of ethyl acetate the mixture is washed with dilute aqueous NaOH or saturated NaHCO3 solution and with water
  2. customdried
  3. customevaporated down
  4. customThe product is crystallised from ethyl acetate/diethylether

Sources & evidence

ORD record
ord-ffde2e1014d34c3ab9ef3e78fbdc4d0a
Source dataset
uspto-grants-2002_06
Patent number
US06407130B1

Reaction notes

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