1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-({[(4-bromo-2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)-N-[4-(pyrrolidin-1-ylmethyl)benzyl]furan-3-carboxamide

HRID 469005Notes

Reaction equation

HRID 469005 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([S:9]([N:12]([CH2:14][C:15]2[O:19][CH:18]=[C:17]([C:20]([OH:22])=O)[CH:16]=2)[CH3:13])(=[O:11])=[O:10])=[C:4]([Cl:23])[CH:3]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[N:45]1([CH2:50][C:51]2[CH:56]=[CH:55][C:54]([CH2:57][NH2:58])=[CH:53][CH:52]=2)[CH2:49][CH2:48][CH2:47][CH2:46]1>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([S:9]([N:12]([CH2:14][C:15]2[O:19][CH:18]=[C:17]([C:20]([NH:58][CH2:57][C:54]3[CH:53]=[CH:52][C:51]([CH2:50][N:45]4[CH2:49][CH2:48][CH2:47][CH2:46]4)=[CH:56][CH:55]=3)=[O:22])[CH:16]=2)[CH3:13])(=[O:11])=[O:10])=[C:4]([Cl:23])[CH:3]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 49628544-(Pyrrolidin-1-ylmethyl)benzylamineHCID 583934255-({[(4-Bromo-2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid

Product 1

HCID 461752845-({[(4-bromo-2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)-N-[4-(pyrrolidin-1-ylmethyl)benzyl]furan-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-({[(4-bromo-2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (40 mg, 0.09 mmol), EDCI (23 mg, 0.12 mmol) and HOBt (15 mg, 0.11 mmol) in DMF (3 mL) was added 1-[4-(pyrrolidin-1-ylmethyl)phenyl]methanamine (17 mg, 0.09 mmol). The reaction was stirred at ambient temperature for 3 days, then absorbed on to an Isolute SCX-2 cartridge, washing with MeOH and eluting the product with 7M NH3 in MeOH. The filtrate was concentrated in vacuo and a portion of the crude product purified using prep method C.

Workup

  1. customabsorbed on to an Isolute SCX-2 cartridge
  2. washwashing with MeOH
  3. washeluting the product with 7M NH3 in MeOH
  4. concentrationThe filtrate was concentrated in vacuo
  5. customa portion of the crude product purified

Sources & evidence

ORD record
ord-324fba865f1c4e49bc7aa907919aba5a
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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