Diisopropylethylamine → HCID 46917718, compound

HRID 1619093Notes

Reaction equation

HRID 1619093 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH:11][C:12]([C:14]1[CH:15]=[C:16]([C:20]2[C:25]([CH3:26])=[CH:24][N:23]=[C:22]([NH:27][C:28]3[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][C:29]=3[CH3:37])[N:21]=2)[N:17]([CH3:19])[CH:18]=1)=[O:13])[CH3:2].C(N(C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:69][N:70]([CH3:77])[CH:71]1[CH2:76][CH2:75][NH:74][CH2:73][CH2:72]1>CN(C)C=O.O>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH:11][C:12]([C:14]1[CH:15]=[C:16]([C:20]2[C:25]([CH3:26])=[CH:24][N:23]=[C:22]([NH:27][C:28]3[CH:36]=[CH:35][C:31]([C:32]([N:74]4[CH2:75][CH2:76][CH:71]([N:70]([CH3:77])[CH3:69])[CH2:72][CH2:73]4)=[O:33])=[CH:30][C:29]=3[CH3:37])[N:21]=2)[N:17]([CH3:19])[CH:18]=1)=[O:13])[CH3:2]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 417391N,N-Dimethylpiperidin-4-amineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 46917644HCID 46917644, compound

Product 1

HCID 46917718HCID 46917718, compoundYield 54.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-{4-[4-(2,6-Diethyl-phenylcarbamoyl)-1-methyl-1H-pyrrol-2-yl]-5-methyl-pyrimidin-2-ylamino}-3-methyl-benzoic acid (177 mg, 0.356 mmol) in anhydrous dimethylformamide (10 mL) was treated with N-ethyl-N,N-diisopropylamine (0.60 mL, 3.55 mmol) and TBTU (183 mg, 0.569 mmol). The mixture was then treated with dimethyl-piperidin-4-yl-amine (91 mg, 0.711 mmol). The reaction was stirred at room temperature for 24 h. The reaction was diluted with water and the resulting precipitate was collected by filtration. The crude solid was purified by flash chromatography on silica gel (eluant: dichloromethane/methanol 9/1) to afford 118 mg of the title compound.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. customThe crude solid was purified by flash chromatography on silica gel (eluant: dichloromethane/methanol 9/1)

Sources & evidence

ORD record
ord-65c7bc84f9854c3d9de397c2e1f96753
Source dataset
uspto-grants-2014_07
Patent number
US08772280B2

Reaction notes

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