Triethylamine → HCID 68648399, compound

HRID 1162598Notes

Reaction equation

HRID 1162598 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][CH2:17][C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)[N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.[CH2:30]([O:32][C:33]([C:35]1[CH:40]=[CH:39][C:38]([N:41]=[C:42]=[O:43])=[CH:37][CH:36]=1)=[O:34])[CH3:31]>C(Cl)Cl>[CH2:30]([O:32][C:33](=[O:34])[C:35]1[CH:40]=[CH:39][C:38]([NH:41][C:42]([N:16]([C:12]2[N:11]=[C:10]([C:7]3[CH:6]=[CH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=3)[CH:15]=[CH:14][N:13]=2)[CH2:17][C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)=[O:43])=[CH:37][CH:36]=1)[CH3:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 589805Ethyl 4-isocyanatobenzoateHCID 68647705HCID 68647705, compound

Product 1

HCID 68648399HCID 68648399, compoundYield 13.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of [4-(4-isopropyl-phenyl)-pyrimidin-2-yl]-thiophen-2-ylmethyl-amine (50 mg, 0.16 mmol) in DCM (2 mL) was added triethylamine (33 μL, 0.24 mmol) and 4-(ethoxycarbonyl)phenyl isocyanate (34 mg, 0.18 mmol). The resulting reaction mixture was heated in a CEM Exployer PLS™ microwave at 100° C. for 30 min. After cooling to room temperature the solvent was evaporated. Purification was carried out by silica gel chromatography eluting with hexanes/ethyl acetate 9:1 to give 11 mg of 4-{3-[4-(4-Isopropyl-phenyl)-pyrimidin-2-yl}-3-thiophen-2-ylmethyl-ureido}-benzoic acid ethyl ester. LCMS m/z: 502 (M+1)+.

Workup

  1. customThe resulting reaction mixture
  2. temperatureAfter cooling to room temperature the solvent
  3. customwas evaporated
  4. customPurification
  5. washeluting with hexanes/ethyl acetate 9:1

Sources & evidence

ORD record
ord-71e0b10a60f14e5692332377addae786
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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