Triethylamine → HCID 23091663, compound

HRID 272940Notes

Reaction equation

HRID 272940 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C([N:8](CC)CC)C.[N:13]1([CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3([CH2:34][NH:35][CH2:36][CH3:37])[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[CH:24][CH:23]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1>ClCCl>[NH3:8].[CH2:36]([N:35]([CH2:34][C:28]1([C:25]2[CH:24]=[CH:23][C:22]([O:21][CH2:20][CH2:19][CH2:18][N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[CH:27][CH:26]=2)[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1)[S:2]([CH3:1])(=[O:4])=[O:3])[CH3:37]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11523085HCID 11523085, compound

Product 2

HCID 222AmmoniaHCID 23091663HCID 23091663, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (19 μL, 0.24 mmol) was added dropwise to a solution of triethylamine (31 μL, 0.22 mmol) and N-({4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-yl}methyl)ethanamine (70 mg, 0.20 mmol) in dichloromethane (0.5 mL) at 0° C. then was allowed to warm to ambient temperature and stirred overnight. The reaction was quenched with NaHCO3 (10 mL), extracted using dichloromethane (3×15 mL), dried using Na2SO4 and concentrated in vacuo. The compound was purified by column chromatography on Biotage® silica gel, eluting with dichloromethane:methanol:ammonia, 96.5:3.5:0.35 to 95:5:0.5 to give the title compound as a pale brown oil (60 mg, 71%). 1H NMR (400 MHz, CDCl3) δ 7.24 (d, 2H), 6.90 (d, 2H), 4.02 (t, 2H), 3.84-3.72 (m, 2H), 3.50 (dt, 2H), 3.28 (s, 2H), 2.72-2.60 (m, 7H), 2.58-2.52 (m, 4H), 2.16 (m, 2H), 2.04 (pentet, 2H), 1.96-1.90 (m, 2H), 1.84-1.76 (m, 4H), 0.90 (t, 3H); HRMS (ESI+) 425.2469 (M+H)+.

Workup

  1. customThe reaction was quenched with NaHCO3 (10 mL)
  2. extractionextracted
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe compound was purified by column chromatography on Biotage® silica gel
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-43465b5d0ca14e73bd33dc2f50415d0c
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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