Diisopropylethylamine → HCID 178464215, compound

HRID 25664Notes

Reaction equation

HRID 25664 reaction equation
Cl.[CH2:2]([N:4]([CH2:19][CH3:20])[C:5](=[O:18])[CH2:6][CH2:7][CH2:8][CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([NH:16][CH3:17])[CH2:12][CH2:11]1)[CH3:3].CCN(C(C)C)C(C)C.[F:30][C:31]([F:43])([F:42])[C:32]1[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:19]([N:4]([CH2:2][CH3:3])[C:5](=[O:18])[CH2:6][CH2:7][CH2:8][CH2:9][C@H:10]1[CH2:11][CH2:12][C@H:13]([N:16]([CH3:17])[S:38]([C:35]2[CH:34]=[CH:33][C:32]([C:31]([F:30])([F:42])[F:43])=[CH:37][CH:36]=2)(=[O:40])=[O:39])[CH2:14][CH2:15]1)[CH3:20]

Participants

6

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 27773994-(Trifluoromethyl)benzenesulfonyl chloride2×HCID 178464213HCID 178464213, compound

Product 1

HCID 178464215HCID 178464215, compoundYield 85.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 6344DichloromethaneSolvent3×

Procedure

0.8 g (2.6 mmol) trans-5-(4-Methylamino-cyclohexyl)-pentanoic acid diethylamide. hydrochloride in 20 ml CH2Cl2 was treated with 1.1 ml (6.3 mmol, 2.4 eq) Huenig's base, 706 mg (2.9 mmol, 1.1 eq) 4-(Trifluoromethyl)benzenesulfonyl chloride in 10 ml CH2Cl2 and 32 mg (0.26 mmol, 0.1 eq) DMAP. The solution was stirred at RT over night. Additonal 1.1 ml (6.3 mmol) Huenig's base, 706 mg (2.9 mmol) 4-(Trifluoromethyl)benzenesulfonyl chloride in 10 ml CH2Cl2 and 32 mg (0.26 mmol) DMAP were added and stirring was continued for 3 h. The mixture was partitioned between CH2Cl2 and a saturated aqueous solution of NaHCO3. The organic phase was washed with water, 1M KHSO4 and brine, dried over Na2SO4 and evaporated. Column chromatography with EtOAc/hexane 1:1 gave 1.06 g (84%) trans-5-{4-[Methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexyl}-pentanoic acid diethylamide as colorless oil, MS: 477 (MH+).

Workup

  1. stirringstirring
  2. customThe mixture was partitioned between CH2Cl2
  3. washThe organic phase was washed with water, 1M KHSO4 and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-eedf320f20b84597b775f57cec664f82
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

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