Triethylamine → HCID 69312125, compound

HRID 2117752Notes

Reaction equation

HRID 2117752 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]([CH3:36])[C:12]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C:22]4[CH:27]=[CH:26][C:25]([S:28](=[O:35])(=[O:34])[NH:29][CH2:30][CH2:31][O:32][CH3:33])=[CH:24][CH:23]=4)[N:16]=3)=[CH:13][N:14]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.CCOC(C)=O>C(O)C.[Pd]>[CH2:9]([C:10]1[N:11]([CH3:36])[C:12]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([S:28](=[O:35])(=[O:34])[NH:29][CH2:30][CH2:31][O:32][CH3:33])=[CH:24][CH:23]=3)[N:16]=2)=[CH:13][N:14]=1)[CH2:8][C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 69311894HCID 69311894, compound

Product 1

HCID 69312125HCID 69312125, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-{2-[2-(4-Chlorophenyl)ethyl]-1-(methyl)imidazol-5-yl}-2-{4-[N-(2-methoxyethyl)sulphamoyl]anilino}pyrimidine (Method 117; 115 mg, 0.219 mmol) and triethylamine (34 μl, 0.241 mmol) was dissolved in ethanol (20 ml) and EtOAc (10 ml) and 30% palladium on charcoal catalyst (30 mg) added. The mixture was stirred for 3 days under an atmosphere of hydrogen. The catalyst was removed by filtration and filtrate evaporated. The residue was dissolved in DCM (20 ml), washed with water (2×5 ml), dried and the solvent removed by evaporation to give the title compound (67 mg, 63%) as a white solid. NMR: 2.88 (q, 2H) 3.05 (s, 4H) 3.16 (s, 3H) 3.28 (t, 3H) 3.90 (s, 3H) 7.21 (d, 1H) 7.28 (m, 5H) 7.69 (s, 1H) 7.70 (d, 2H) 8.44 (d, 1H) 9.94 (s, 1H); m/z 493.

Workup

  1. customThe catalyst was removed by filtration and filtrate
  2. customevaporated
  3. dissolutionThe residue was dissolved in DCM (20 ml)
  4. washwashed with water (2×5 ml)
  5. customdried
  6. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-b0789aaa50d9459985dda95d34f7f11d
Source dataset
uspto-grants-2008_10
Patent number
US07442697B2

Reaction notes

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