Diisopropylethylamine → HCID 57664570, compound

HRID 1467880Notes

Reaction equation

HRID 1467880 reaction equation
[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.[CH2:24]([O:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1)[CH2:25][CH2:26][CH3:27].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:24]([O:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([N:21]2[CH2:22][CH2:23][CH:18]([N:4]([CH:1]3[CH2:3][CH2:2]3)[S:5]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=3)(=[O:6])=[O:7])[CH2:19][CH2:20]2)(=[O:37])=[O:36])=[CH:31][CH:30]=1)[CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5179904-Butoxybenzenesulfonyl ChlorideHCID 2773944N-Cyclopropyl-N-piperidin-4-yl-3-(trifluoromethyl)benzenesulfonamide

Product 1

HCID 57664570HCID 57664570, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

150 mg (0.434 mmol) of N-cyclopropyl-N-piperidin-4-yl-3-trifluoromethylbenzenesulfonamide (available from Lancaster) and 108 mg (0.434 mmol) of 4-butoxyphenylsulfonyl chloride (available from Matrix Scientific) were each dissolved in 10 mL of DCM and then combined. 1.5 eq. of DIEA (0.113 mL) was added to the mixture by syringe. The mixture was stirred overnight at room temperature and then concentrated under vacuum. The resultant product 29 was purified through a column of silica gel with a gradient of 0% to 20% EtOAc in hexanes and the pure material was concentrated (yield 25%, white solid). 1H NMR (CDCl3): δ 8.058 (s, 1H), 8.003-7.983 (d, 1H), 7.851-7.831 (d, 1H), 7.688-7.641 (m, 3H), 7.017-6.980 (m, 2H), 4.055-4.022 (t, 2H), 3.843-3.746 (m, 3H), 2.286-2.226 (t, 2H), 2.068-1.901 (m, 3H), 1.843-1.773 (m, 2H), 1.6151-1.470 (m, 4H), 1.014-0.976 (t, 3H), 0.944-0.903 (m, 2H), 0.793-0.744 (m, 2H). LC: 100%. MS (e/z): 562 (M+H+).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe resultant product 29 was purified through a column of silica gel with a gradient of 0% to 20% EtOAc in hexanes
  3. concentrationthe pure material was concentrated (yield 25%, white solid)

Sources & evidence

ORD record
ord-02f1a3d68a684ad98ecadb5e6fa1ab1e
Source dataset
uspto-grants-2015_04
Patent number
US09000174B2

Reaction notes

Loading…