Triethylamine → HCID 23091632, compound

HRID 272941Notes

Reaction equation

HRID 272941 reaction equation
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].C([N:9](CC)CC)C.[N:14]1([CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3([CH2:35][NH:36][CH2:37][CH3:38])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[CH:25][CH:24]=2)[CH2:18][CH2:17][CH2:16][CH2:15]1>ClCCl>[NH3:9].[CH2:37]([N:36]([CH2:35][C:29]1([C:26]2[CH:25]=[CH:24][C:23]([O:22][CH2:21][CH2:20][CH2:19][N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:28][CH:27]=2)[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1)[S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH3:38]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 11523085HCID 11523085, compound

Product 2

HCID 222AmmoniaHCID 23091632HCID 23091632, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethanesulfonyl chloride (26 μL, 0.28 mmol) was added dropwise to a solution of triethylamine (35 μL, 0.25 mmol) and N-({4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-yl}methyl)ethanamine (78 mg, 0.23 mmol) in dichloromethane (0.5 mL) at 0° C. allowed to warm to ambient temperature and stirred overnight. The reaction was quenched with NaHCO3 (10 mL), extracted using dichloromethane (3×10 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 (55 mg, 54%). 1H NMR (400 MHz, CDCl3) δ 7.24 (d, 2H), 6.90 (d, 2H), 4.02 (t, 2H), 3.84-3.72 (m, 2H), 3.48 (t, 2H), 3.32 (s, 2H), 2.76 (quartet, 2H), 2.72-2.60 (m, 4H), 2.60-2.48 (m, 4H), 2.20-2.08 (m, 2H), 2.04 (pentet, 2H), 1.98-1.90 (m, 2H), 1.86-1.76 (m, 4H), 1.30 (t, 3H), 0.88 (t, 3H). HRMS (ESI+) 439.2625 (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-5a87143d99e043eeb776afdf20f40272
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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