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N,N-Dimethylglycine → 1-{4-[3-({1-[Bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazin-1-yl}-2-dimethylaminoethanone

HRID 25232
Notes
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Reaction equation

HRID 25232 reaction equation
CCN=C=NCCCN(C)C.[CH3:12][N:13]([CH3:18])[CH2:14][C:15](O)=[O:16].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]([C:48]2[CH:53]=[CH:52][C:51]([Cl:54])=[CH:50][CH:49]=2)[N:27]2[CH2:30][C:29](=[CH:31][S:32]([CH2:35][C:36]3[CH:37]=[C:38]([N:42]4[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]4)[CH:39]=[CH:40][CH:41]=3)(=[O:34])=[O:33])[CH2:28]2)=[CH:22][CH:21]=1>ClCCl>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([CH:26]([C:48]2[CH:49]=[CH:50][C:51]([Cl:54])=[CH:52][CH:53]=2)[N:27]2[CH2:28][C:29](=[CH:31][S:32]([CH2:35][C:36]3[CH:37]=[C:38]([N:42]4[CH2:47][CH2:46][N:45]([C:15](=[O:16])[CH2:14][N:13]([CH3:18])[CH3:12])[CH2:44][CH2:43]4)[CH:39]=[CH:40][CH:41]=3)(=[O:33])=[O:34])[CH2:30]2)=[CH:24][CH:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 673N,N-Dimethylglycine2×HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 696356951-[3-({1-[Bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazine

Product 1

HCID 186687351-{4-[3-({1-[Bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazin-1-yl}-2-dimethylaminoethanoneYield 84.8%

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent

Procedure

511 mg of supported EDCI (2.5 mM), 11.5 mg of N,N-dimethylglycine and then 5 cm3 of dichloromethane are successively added, at a temperature close to 20° C., to 54 mg of 1-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazine. After stirring for 24 hours at a temperature close to 20° C., 35 mg of N,N-dimethylglycine are added. After stirring for 96 hours at a temperature close to 20° C., the reaction mixture is filtered on sintered glass. The resin is rinsed with three times 2.5 cm3 of dichloromethane. The combined filtrates are washed with 10 cm3 of water, dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (5 kPa) at a temperature close to 20° C. 53 mg of 1-{4-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazin-1-yl}-2-dimethylaminoethanone are thus obtained in the form of a beige foam [1H NMR spectrum (400 MHz, (CD3)2SO-d6, δ in ppm): 2.20 (s, 6H), 2.94 (s, 3H), 3.12 (s, 2H), 3.16 (mt, 4H), 3.58 (mt, 2H), 3.68 (mt, 2H), 3.80 (mt, 2H), 4.19 (mt, 2H), 4.78 (s, 1H), 6.81 (broad d, J=8 Hz, 1H), 6.93 (broad s, 1H), 6.99 (dd, J=8 and 2.5 Hz, 1H), 7.26 (t, J=8 Hz, 1H), 7.36 (d, J=8 Hz, 4H), 7.46 (d, J=8 Hz, 4H)].

Workup

  1. customclose to 20° C.
  2. stirringAfter stirring for 96 hours at a temperature
  3. customclose to 20° C.
  4. filtrationthe reaction mixture is filtered on sintered glass
  5. washThe resin is rinsed with three times 2.5 cm3 of dichloromethane
  6. washThe combined filtrates are washed with 10 cm3 of water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (5 kPa) at a temperature
  10. customclose to 20° C

Sources & evidence

ORD record
ord-3744df2ec649460a8c20ac0130a246e1
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06858603B2

Reaction notes

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