Water → HCID 18426156, compound

HRID 1281037Notes

Reaction equation

HRID 1281037 reaction equation
Cl[C:2]([C:4]1[CH:34]=[CH:33][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][NH:16][C:17](=[O:32])[CH2:18][NH:19][C:20](=[O:31])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[CH2:11][CH2:10]2)=[CH:6][CH:5]=1)=[O:3].[CH3:35][O:36][CH2:37][CH2:38][NH2:39].ClCCl.O>CO>[CH3:35][O:36][CH2:37][CH2:38][NH:39][C:2]([C:4]1[CH:34]=[CH:33][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][NH:16][C:17](=[O:32])[CH2:18][NH:19][C:20](=[O:31])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[CH2:11][CH2:10]2)=[CH:6][CH:5]=1)=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 80182-MethoxyethylamineHCID 18426175HCID 18426175, compound

Product 1

HCID 18426156HCID 18426156, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-[4-(chloroformyl)benzyl]-4-[{N-(3-(trifluoromethyl)benzoyl)glycyl}aminomethyl]piperidine (0.042 mmol), 2-methoxyethylamine (3.8 mg, 0.050 mmol), piperidinomethylpolystyrene (46 mg) and dichloromethane (1.5 mL) was stirred at room temperature for 17 h. Water (0.020 mL) was added and the mixture was stirred for 30 min. Methanol (1 mL) was added and the mixture was loaded onto Varian™ SCX column, and washed with CH3OH (10 mL). Product was eluted off using 2 N NH3 in CH3OH (5 mL) and concentrated to afford 1-[4-{N-(2-methoxyethyl)carbamoyl}benzyl]-4-[{N-(3-(trifluoromethyl)benzoyl)glycyl}aminomethyl]piperidine (Compound No. 1612) (26.7 mg, 100%): The purity was determined by RPLC/MS (92%); ESI/MS m/e 535.2 (M−+H, C27H33F3N4O4).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. washwashed with CH3OH (10 mL)
  3. washProduct was eluted off
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cf33f4be3dd142a0baa8ff169ea95035
Source dataset
uspto-grants-2002_09
Patent number
US06451842B1

Reaction notes

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