Diisopropylethylamine → HCID 57664573, compound

HRID 1467879Notes

Reaction equation

HRID 1467879 reaction equation
[CH:1]1([N:4]([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.[CH2:20]([O:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1)[CH2:21][CH2:22][CH3:23].CCN(C(C)C)C(C)C>ClCCl>[CH2:20]([O:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([N:17]2[CH2:18][CH2:19][CH:14]([N:4]([CH:1]3[CH2:3][CH2:2]3)[S:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)(=[O:6])=[O:7])[CH2:15][CH2:16]2)(=[O:33])=[O:32])=[CH:27][CH:26]=1)[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5179904-Butoxybenzenesulfonyl ChlorideHCID 2735904387350-82-5

Product 1

HCID 57664573HCID 57664573, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

143 mg (0.513 mmol) of N-cyclopropyl-N-piperidin-4-yl-benzenesulfonamide (available from Lancaster) and 128 mg (0.513 mmol) of 4-butoxyphenylsulfonyl chloride (available from Matrix Scientific) were each dissolved in 5 mL dichloromethane (DCM) and then combined. 1.5 eq. of diisoprolylethylamine (DIEA) (0.134 mL) was added to the mixture by syringe. The mixture was stirred overnight at room temperature and then concentrated under vacuum. The resultant product 27 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 24%, white solid). 1H NMR (CDCl3): δ 7.813-7.783 (m, 2H), 7.673-7.636 (m, 2H), 7.597-7.553 (m, 1H), 7.520-7.475 (m, 2H), 7.011-6.974 (m, 2H), 4.053-4.020 (t, 2H), 3.821-3.721 (m, 3H), 2.266-2.200 (t, 2H), 2.033-1.902 (m, 3H), 1.843-1.779 (m, 2H), 1.601-1.470 (m, 4H), 1.015-0.978 (t, 3H), 0.935-0.896 (m, 2H), 0.761-0.712 (m, 2H). LC: 100%. MS (e/z): 494 (M+H+).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe resultant product 27 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 24%, white solid)

Sources & evidence

ORD record
ord-f1d0a21bc0d34aa39772f264b7506bf8
Source dataset
uspto-grants-2015_04
Patent number
US09000174B2

Reaction notes

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