Triethylamine → HCID 24936315, compound

HRID 561032Notes

Reaction equation

HRID 561032 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]3[C:13]([C:17]4[CH:22]=[C:21]([F:23])[N:20]=[CH:19][C:18]=4[CH2:24][N:25]([CH3:27])[CH3:26])=[CH:14][CH:15]=[CH:16][C:10]=3[CH:9]=2)[C:5]([F:28])=[CH:4][N:3]=1.C(N(CC)CC)C.[NH2:36][CH2:37][CH2:38][N:39]1[CH2:43][CH2:42][NH:41][C:40]1=[O:44]>C(O)CCC.C(OCC)(=O)C>[CH3:26][N:25]([CH2:24][C:18]1[C:17]([C:13]2[C:11]3[S:12][C:8]([C:6]4[C:5]([F:28])=[CH:4][N:3]=[C:2]([NH:36][CH2:37][CH2:38][N:39]5[CH2:43][CH2:42][NH:41][C:40]5=[O:44])[N:7]=4)=[CH:9][C:10]=3[CH:16]=[CH:15][CH:14]=2)=[CH:22][C:21]([F:23])=[N:20][CH:19]=1)[CH3:27]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 80480N-(2-Aminoethyl)ethyleneureaHCID 86640500HCID 86640500, compound

Product 1

HCID 24936315HCID 24936315, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

Combine {4-[2-(2-chloro-5-fluoro-pyrimidin-4-yl)-benzo[b]thiophen-7-yl]-6-fluoro-pyridin-3-ylmethyl}-dimethyl-amine (0.25 g, 0.59 mmol) and triethylamine (0.25 mL, 1.78 mmol) in n-butanol (8.0 mL). Add 1-(2-aminoethyl) imidazolidin-2-one (0.23 g, 1.78 mmol). Heat the reaction mixture at 120° C. overnight (15 hours), then cool to room temperature. Dilute the reaction mixture with ethyl acetate, and wash with water and saturated aqueous sodium chloride. Separate the organic layer from aqueous layer and dry over MgSO4. After filtration, remove the organic solvent to give a crude. Purify the crude by column chromatography (0.5% to 10% 2 N NH3 in methanol solution/dichloromethane) to afford the title compound (0.19 g, 63%). MS (ES) m/z 510 [M+1]+.

Workup

  1. temperaturecool to room temperature
  2. washwash with water and saturated aqueous sodium chloride
  3. customSeparate the organic layer from aqueous layer
  4. dry with materialdry over MgSO4
  5. filtrationAfter filtration
  6. customremove the organic solvent
  7. customto give a crude
  8. customPurify the crude by column chromatography (0.5% to 10% 2 N NH3 in methanol solution/dichloromethane)

Sources & evidence

ORD record
ord-c47ecd8e57ab4814bd5933b611023773
Source dataset
uspto-grants-2011_11
Patent number
US08063212B2

Reaction notes

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