Triethylamine → HCID 18448528, compound

HRID 1269461Notes

Reaction equation

HRID 1269461 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][C:8]([NH:10][CH:11]1[C:20]2[C:15](=[CH:16][C:17]([C:21]([CH2:23][N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH2:22])=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1)=[O:9].[F:30][C:31]([F:43])([F:42])[C:32]1[CH:33]=[C:34]([S:38](Cl)(=[O:40])=[O:39])[CH:35]=[CH:36][CH:37]=1.CCN(CC)CC>C(Cl)Cl>[N:24]1([CH2:23][C:21]([C:17]2[CH:16]=[C:15]3[C:20](=[CH:19][CH:18]=2)[CH:11]([NH:10][C:8](=[O:9])[CH2:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][N:1]2[S:38]([C:34]2[CH:35]=[CH:36][CH:37]=[C:32]([C:31]([F:30])([F:42])[F:43])[CH:33]=2)(=[O:40])=[O:39])[CH2:12][CH2:13][CH2:14]3)=[CH2:22])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 18448583HCID 18448583, compound

Product 1

HCID 18448528HCID 18448528, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-piperidin-2-yl-N-[6-(1-piperidin-1-ylmethyl-vinyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-acetamide (155.8 mg, 0.39 mmol) in CH2Cl2(2 mL) was added 3-(trifluoromethyl)benzenesulfonyl chloride (Fluka, 0.1 mL, 0.59 mmol) and Et3N (Aldrich, 0.1 mL, 0.79 mmol). The mixture was stirred at rt overnight, diluted with CH2Cl2 (30 mL), washed with 10% Na2CO3 (twice) and brine. The organic solution was dried over Na2SO4, filtered and concentrated in vacuo. The crude was purified by silica gel chromatography (3%–10% MeOH—CH2Cl2) to provide the title compound. MS (ESI): 604 (M+H)+. Calc'd for C32H40F3N3O3S—603.27.

Workup

  1. washwashed with 10% Na2CO3 (twice) and brine
  2. dry with materialThe organic solution was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude was purified by silica gel chromatography (3%–10% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-40f147b68bfb4c58885b34d19dcc5d01
Source dataset
uspto-grants-2007_04
Patent number
US07199244B2

Reaction notes

Loading…