Triethylamine → HCID 68647843, compound

HRID 1162599Notes

Reaction equation

HRID 1162599 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.[N:30]([C:33]1[CH:42]=[CH:41][CH:40]=[CH:39][C:34]=1[C:35]([O:37][CH3:38])=[O:36])=[C:31]=[O:32]>C(Cl)Cl>[CH3:38][O:37][C:35](=[O:36])[C:34]1[CH:39]=[CH:40][CH:41]=[CH:42][C:33]=1[NH:30][C:31]([N:16]([C:12]1[N:11]=[C:10]([C:7]2[CH:6]=[CH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=2)[CH:15]=[CH:14][N:13]=1)[CH2:17][C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 519494Methyl 2-isocyanatobenzoateHCID 68647705HCID 68647705, compound

Product 1

HCID 68647843HCID 68647843, compoundYield 2.6%

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 methyl 2-isocyanatobenzoate (32 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 2 mg of 2-{3-[4-(4-isopropyl-phenyl)-pyrimidin-2-yl}-3-thiophen-2-ylmethyl-ureido}-benzoic acid methyl ester. LCMS m/z: 488 (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-630c1fbed5ab4e17ae06f75e6e93116d
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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