Triethylamine → HCID 18426139, compound

HRID 279348Notes

Reaction equation

HRID 279348 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), methanesulfonyl chloride (0.0045 mL), triethylamine (0.026 mL) and dichloromethane (2 mL) was stirred at room temperature for 17 h. The reaction mixture was purified with column chromatography (SiO2), loaded onto Varian™ SAX column, and washed with CH3OH (5 mL). Product was eluted off using 0.1 N HCl in CH3OH (5 mL) and concentrated to afford 4-[{N-(5-bromo-2-(methylsulfonylamino)benzoyl)glycyl}aminomethyl]-1-(4-chlorobenzyl)piperidine (Compound No. 1581) (5.4 mg, 19%): ESI/MS m/e 573.0 (M++H, C23H28BrClN4O4S).

Workup

  1. customThe reaction mixture was purified with column chromatography (SiO2)
  2. washwashed with CH3OH (5 mL)
  3. washProduct was eluted off
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-11dbdd02744c4733ba68845685bf0151
Source dataset
uspto-grants-2002_03
Patent number
US06362177B1

Reaction notes

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