Water → HCID 18426156, compound

HRID 133623Notes

Reaction equation

HRID 133623 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) with 2-methoxyethylamine (3.8 mg, 0.050 mmol), a piperidinomethylpolystyrene (46 mg) and dichloromethane (1.5 mL) was stirred at room temperature for 17 hours. Water (0.020 mL) was then added to the mixture, and the resulting mixture was stirred for 30 minutes. Methanol (1 mL) was then added to the obtained mixture, and the resulting mixture was loaded onto a Varian™ SCX column and washed with methanol (10 mL). The obtained crude product was eluted with a 2 M methanol solution of NH3 and concentrated to thereby provide 1-[4-[N-(2-methoxyethyl)carbamoyl]benzyl]-4-[[N-(3-(trifluoromethyl)benzoyl)glycyl]aminomethyl]piperidine (Compd. 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. washwashed with methanol (10 mL)
  2. customThe obtained crude product
  3. washwas eluted with a 2 M methanol solution of NH3
  4. concentrationconcentrated to thereby provide 1-[4-[N-(2-methoxyethyl)carbamoyl]benzyl]-4-[[N-(3-(trifluoromethyl)benzoyl)glycyl]aminomethyl]piperidine (Compd. No

Sources & evidence

ORD record
ord-848e168848334a7cb15a4ccdb1ad7b93
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

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