Diisopropylethylamine → HCID 86674092, compound

HRID 337238Notes

Reaction equation

HRID 337238 reaction equation
C(N(C(C)C)CC)(C)C.[C:10]([O:14][C:15](=[O:23])[NH:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)([CH3:13])([CH3:12])[CH3:11].[Cl:24][C:25]1[N:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1>C(Cl)Cl>[C:10]([O:14][C:15](=[O:23])[NH:16][CH:17]1[CH2:22][CH2:21][N:20]([S:31]([C:28]2[CH:29]=[N:30][C:25]([Cl:24])=[CH:26][CH:27]=2)(=[O:33])=[O:32])[CH2:19][CH2:18]1)([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 7238334-(N-Boc-amino)piperidineHCID 27927922-Chloro-5-pyridinesulfonyl chloride

Product 1

HCID 86674092HCID 86674092, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diisopropylethylamine (1.34 ml, 8.14 mmol) was added in one portion to a stirred solution of piperidin-4-yl-carbamic acid tert-butyl ester (0.5 g, 2.70 mmol) in DCM (20 ml) at room temperature. To this mixture was added 6-chloro-pyridine-3-sulfonyl chloride (0.57 g, 2.70 mmol) in one portion and the mixture was stirred at room temperature under a nitrogen atmosphere for 1 hour. After this time the mixture was diluted with DCM (50 ml) and washed sequentially with HCl (1M solution, 20 ml), NaOH (1M solution, 20 ml) and brine (20 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated to give the title compound (0.64 g, 65% yield) as a white solid. δH (500 MHz, DMSO) 8.76 (d, J=2.20 Hz, 1 H) 8.19 (dd, J=8.44, 2.57 Hz, 1 H) 7.82 (d, J=8.44 Hz, 1 H) 6.89 (d, J=7.70 Hz, 1 H) 3.48 (d, J=11.92 Hz, 2 H) 3.31 (br. s., 1 H) 2.59-2.68 (m, 2 H) 1.76 (d, J=10.27 Hz, 2 H) 1.30-1.46 (m, 11 H).

Workup

  1. washwashed sequentially with HCl (1M solution, 20 ml), NaOH (1M solution, 20 ml) and brine (20 ml)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-00a3dbeb5aa54a0e8f838bb8843f8472
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

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