Triethylamine → HCID 131728656, compound

HRID 1363026Notes

Reaction equation

HRID 1363026 reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([O:15][CH:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][NH2:25])[CH2:18][CH2:17]3)[CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2)[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.[CH2:33]([S:35]([Cl:38])(=[O:37])=[O:36])[CH3:34]>C(Cl)Cl.CO>[ClH:38].[ClH:38].[CH2:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([O:15][CH:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][NH:25][S:35]([CH2:33][CH3:34])(=[O:37])=[O:36])[CH2:18][CH2:17]3)[CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 66921928HCID 66921928, compound2×

Product 1

HCID 131728656HCID 131728656, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

(3-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}propyl)amine (for example, as prepared for Intermediate 36) (30 mg, 0.09 mmol) was dissolved in DCM (1 ml), and treated with triethylamine (38 μl, 0.27 mmol), and ethanesulfonyl chloride (commercially available, for example, from Aldrich) (17 μl, 0.18 mmol). The mixture was stirred in a stoppered vial at room temperature for 1 h, then left to stand at room temperature overnight. The mixture was diluted with methanol and applied to an SCX-2 cartridge (5 g) eluting with methanol, followed by 10% aqueous 0.88 s.g. ammonia in methanol. The relevant fractions were concentrated, and the residue was purified by MDAP. The appropriate fractions were combined and concentrated to give the title compound as the monoformate salt (29 mg, 67%): LCMS RT=2.62 min, ES+ve m/z 434 (M+H)+. The material was dissolved in methanol and treated with 1.25 M hydrogen chloride in methanol (excess). The volatiles were removed under a stream of nitrogen to give the title compound (30 mg): LCMS RT=2.63 min, ES+ve m/z 434 (M+H)+.

Workup

  1. waitleft
  2. waitto stand at room temperature overnight
  3. washeluting with methanol
  4. customfollowed by 10% aqueous 0.88 s
  5. concentrationThe relevant fractions were concentrated
  6. customthe residue was purified by MDAP
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-dce69cf5ae5b4077b43d317975192098
Source dataset
uspto-grants-2011_02
Patent number
US07884114B2

Reaction notes

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