Triethylamine → HCID 21023791, compound

HRID 1795151Notes

Reaction equation

HRID 1795151 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:19]([CH3:28])([CH3:27])[CH2:20][NH:21][S:22]([CH:25]=[CH2:26])(=[O:24])=[O:23])[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][C:3]=1[O:29]C.[CH:31](S(Cl)(=O)=O)=[CH2:32].ClC1C=CC([C:44]2[N:45]=[C:46](C(C)(C)CN)[NH:47][C:48]=2C2C=CN=CC=2)=CC=1OC.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:19]([CH3:28])([CH3:27])[CH2:20][NH:21][S:22]([CH2:25][CH2:26][N:47]3[CH2:32][CH2:31][N:45]([CH3:46])[CH2:44][CH2:48]3)(=[O:24])=[O:23])[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][C:3]=1[OH:29]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5334456608-47-5HCID 22185381HCID 22185381, compoundHCID 86759974HCID 86759974, compound

Product 1

HCID 21023791HCID 21023791, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethensulfonic acid {2-[4-(4-chloro-3-methoxy-phenyl)-5-pyridin-4-yl-1H-imidazol-2-yl]-2-methyl-propyl}-amide A solution of ethenesulfonyl chloride (J. Marchand-Brynaert et al., Tetrahedron 1966, 52, 5591) (230 mg, 1.8 mmol) in dichloromethane (10 ml) was cooled to −78° C. and treated with a solution of the product of Example 2 and triethylamine (0.4 ml, 3 mmol) in dichloromethane (10 ml). After 1 hour the reaction mixture was warmed to room temperature and the solution washed with saturated sodium hydrogen carbonate solution. The organic layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate, filtered and the solvent evaporated to give the title compound (254 mg, 38%); MS(ES+) m/e 447/449 [M+H]+. Step 2. 2-(4-Methyl-piperazin-1-yl)-ethanesulfonic acid {2-[4-(4-chloro-3-methoxy-phenyl)-5-pyridin-4-yl-1H-imidazol-2-yl]-2-methyl-propyl}-amide A solution of the produce of Step 1 (110 mg, 0.25 mmol) and N-methylpiperazine (50 mg, 0.5 mmol) in dichloromethane (5 ml) was stirred at room temperature for 72 hours. The solvent was evaporated and the residue was purified by silica gel chromatography to give the title compound (98 mg, 72%); MS(ES+) m/e 547/549 [M+H]+. Step 3. 2-(4-Methyl-piperazin-1-yl)-ethanesulfonic acid {2-[4-(4-chloro-3-hydroxy-phenyl)-5-pyridin-4-yl-1H-imidazol-2-yl]-2-methyl-propyl}-amide The title compound was prepared from the product of Step 2 using the method described in Example 3 and the product purified by silica gel chromatography; MS(ES+) m/e 533/535 [M+H]+.

Workup

  1. washthe solution washed with saturated sodium hydrogen carbonate solution
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-6e6f36a782034b18846eb1bfa1e45393
Source dataset
uspto-grants-2006_04
Patent number
US07026336B1

Reaction notes

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