Triethylamine → N-{3-[4-(4-Acetyl-2-fluoro-phenyl)-piperazine-1-carbonyl]-4-morpholin-4-yl-phenyl}-methanesulfonamide

HRID 736188Notes

Reaction equation

HRID 736188 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[C:6]([CH:25]=1)[C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:23])[CH3:22])=[CH:17][C:16]=2[F:24])[CH2:11][CH2:10]1)=[O:8].C(N(CC)CC)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>O1CCOCC1.O>[C:21]([C:18]1[CH:19]=[CH:20][C:15]([N:12]2[CH2:11][CH2:10][N:9]([C:7]([C:6]3[CH:25]=[C:2]([NH:1][S:40]([CH3:39])(=[O:42])=[O:41])[CH:3]=[CH:4][C:5]=3[N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)=[O:8])[CH2:14][CH2:13]2)=[C:16]([F:24])[CH:17]=1)(=[O:23])[CH3:22]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 44580511HCID 44580511, compound

Product 1

HCID 59793624N-{3-[4-(4-Acetyl-2-fluoro-phenyl)-piperazine-1-carbonyl]-4-morpholin-4-yl-phenyl}-methanesulfonamideYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 1-{4-[4-(5-Amino-2-morpholin-4-yl-benzoyl)-piperazin-1-yl]-3-fluoro-phenyl}-ethanone (50 mg, 0.12 mmol) and triethylamine (33 ul, 0.234 mmol) in dioxane (1.5 ml) was added a solution of methanesulfonyl chloride (15 mg, 0.13 mmol) in dioxane (0.5 ml). The mixture was stirred at room temperature for 3 hours. The reaction mixture was stirred in water. The yellow solid was filtered, washed with water and dissolved in CH2Cl2. The solution was dried over Na2SO4, filtered and the solvent was removed in vacuo. The residue was chromatographed over silica gel eluent: Heptane/ethyl acetate 0%-100% (5 minutes) to provide the title compound (35 mg, 59%) as a yellow solid MS (m/e): 505.3 (M+H, 100%)

Workup

  1. filtrationThe yellow solid was filtered
  2. washwashed with water
  3. dissolutiondissolved in CH2Cl2
  4. dry with materialThe solution was dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe residue was chromatographed over silica gel eluent

Sources & evidence

ORD record
ord-ccf0d462edc74dac8e8075eca00a9d8e
Source dataset
uspto-grants-2009_09
Patent number
US07595314B2

Reaction notes

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