Triethylamine → HCID 18426139, compound

HRID 133626Notes

Reaction equation

HRID 133626 reaction equation
[NH2:1][C:2]1[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][C:3]=1[C:4]([NH:6][CH2:7][C:8]([NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)=[O:9])=[O:5].[CH3:31][S:32](Cl)(=[O:34])=[O:33].C(N(CC)CC)C>ClCCl>[Br:30][C:27]1[CH:28]=[CH:29][C:2]([NH:1][S:32]([CH3:31])(=[O:34])=[O:33])=[C:3]([CH:26]=1)[C:4]([NH:6][CH2:7][C:8]([NH:10][CH2:11][CH:12]1[CH2:13][CH2:14][N:15]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=2)[CH2:16][CH2:17]1)=[O:9])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 508820HCID 508820, compound

Product 1

HCID 18426139HCID 18426139, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[[N-[2-amino-5-bromobenzoyl]glycyl]aminomethyl]-1-(4-chlorobenzyl)piperidine (25 mg, 0.05 mmol) with methanesulfonyl chloride (0.0045 mL), triethylamine (0.026 mL) and dichloromethane (2 mL) was stirred at room temperature for 17 hours. The resulting reaction mixture was purified by column chromatography (SiO2), loaded onto a Varian™ SAX column and washed with methanol (5 mL). The obtained crude product was eluted with a 0.1 M methanol solution of HCl (5 mL) and concentrated to thereby provide 4-[[N-[5-bromo-2-(methylsulfonylamino)benzoyl]glycyl]aminomethyl]-1-(4-chlorobenzyl)piperidine (Compd. No. 1581) (5.4 mg, 19%). ESI/MS m/e 573.0 (M++H, C23H28BrClN4O4S).

Workup

  1. customThe resulting reaction mixture
  2. customwas purified by column chromatography (SiO2)
  3. washwashed with methanol (5 mL)
  4. customThe obtained crude product
  5. washwas eluted with a 0.1 M methanol solution of HCl (5 mL)
  6. concentrationconcentrated to thereby provide 4-[[N-[5-bromo-2-(methylsulfonylamino)benzoyl]glycyl]aminomethyl]-1-(4-chlorobenzyl)piperidine (Compd. No

Sources & evidence

ORD record
ord-af628a02d5b34778a767b08a6613d164
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

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