Triethylamine → HCID 59714954, compound

HRID 2223903Notes

Reaction equation

HRID 2223903 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([N:18]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)[C:19]([C:21]3[O:22][CH:23]=[CH:24][CH:25]=3)=[O:20])[CH2:14][CH2:13]2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.C(N(CC)CC)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>ClCCl>[CH3:40][S:41]([NH:1][CH2:2][CH2:3][C:4]1([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([N:18]([C:26]3[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=3)[C:19]([C:21]3[O:22][CH:23]=[CH:24][CH:25]=3)=[O:20])[CH2:14][CH2:13]2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)(=[O:43])=[O:42]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23109894HCID 23109894, compound

Product 1

HCID 59714954HCID 59714954, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[1-[2-[1-(2-aminoethyl) cyclohexyl]ethyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamide (synthesized in Example 18) (260 mg) in dichloromethane (3 mL) were added triethylamine (0.15 mL) and methanesulfonyl chloride (56 μL) successively. The solution was stirred at room temperature for 6 hours. The reaction solution was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by chromatography [NH silica gel, hexane-ethyl acetate (7:3 to 1:1 to 1:2] to give the title compound (214 mg).

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by chromatography [NH silica gel, hexane-ethyl acetate (7:3 to 1:1 to 1:2]

Sources & evidence

ORD record
ord-c6503fc0fbc34b55ab58a9dfbe7bb696
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

Loading…