N-(3-Aminopropyl)morpholine → 3-({1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene} methanesulfonylmethyl)-N-(3-morpholin-4-ylpropyl)benzamide

HRID 25207

Reaction equation

HRID 25207 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=2)[N:19]2[CH2:22][C:21](=[CH:23][S:24]([CH2:27][C:28]3[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=3)[C:31](O)=[O:32])(=[O:26])=[O:25])[CH2:20]2)=[CH:14][CH:13]=1>ClCCl>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([C:37]2[CH:38]=[CH:39][C:40]([Cl:43])=[CH:41][CH:42]=2)[N:19]2[CH2:22][C:21](=[CH:23][S:24]([CH2:27][C:28]3[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=3)[C:31]([NH:1][CH2:2][CH2:3][CH2:4][N:5]3[CH2:10][CH2:9][O:8][CH2:7][CH2:6]3)=[O:32])(=[O:26])=[O:25])[CH2:20]2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 61055N-(3-Aminopropyl)morpholineHCID 696356783-({1-[Bis(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)benzoic acid

Product 1

HCID 696356533-({1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene} methanesulfonylmethyl)-N-(3-morpholin-4-ylpropyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.0388 cm3 of N-(3-aminopropyl)morpholine is added, at the same temperature, to a suspension of 150 mg of 3-({1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)benzoic acid activated on TFP resin (165 μM) in 3 cm3 of dichloromethane, pre-stirred for 90 minutes at a temperature close to 20° C. The suspension is stirred at a temperature close to 20° C. for 22 hours and then filtered on sintered glass. The solid residue is rewashed with twice 1.5 cm3 of dichloromethane. The filtrates are combined and concentrated to dryness under reduced pressure (2.7 kPa) at a temperature close to 40° C. 60 mg of 3-({1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)-N-(3-morpholin-4-ylpropyl)benzamide are thus obtained in the form of a pale yellow foam.

Workup

  1. customclose to 20° C
  2. stirringThe suspension is stirred at a temperature
  3. customclose to 20° C. for 22 hours
  4. filtrationfiltered on sintered glass
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at a temperature
  6. customclose to 40° C

Sources & evidence

ORD record
ord-4634c880f5ca4716bd33fcdc4904024b
Source dataset
uspto-grants-2005_02
Patent number
US06858603B2

Linked notes

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