1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-N-(1,2,2,6,6-pentamethylpiperidin-4-yl)furan-3-carboxamide

HRID 468983Notes

Reaction equation

HRID 468983 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]([CH2:15][C:16]2[O:20][CH:19]=[C:18]([C:21](O)=[O:22])[CH:17]=2)[CH3:14])(=[O:12])=[O:11])=[C:5]([CH3:24])[CH:4]=1.[CH:25]1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH3:46][C:47]1([CH3:56])[CH2:52][CH:51]([NH2:53])[CH2:50][C:49]([CH3:55])([CH3:54])[NH:48]1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]([CH2:15][C:16]2[O:20][CH:19]=[C:18]([C:21]([NH:53][CH:51]3[CH2:50][C:49]([CH3:55])([CH3:54])[N:48]([CH3:25])[C:47]([CH3:56])([CH3:46])[CH2:52]3)=[O:22])[CH:17]=2)[CH3:14])(=[O:11])=[O:12])=[C:5]([CH3:24])[CH:4]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 375244-Amino-2,2,6,6-tetramethylpiperidineHCID 757711-HydroxybenzotriazoleHCID 583930975-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid

Product 1

HCID 461759795-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-N-(1,2,2,6,6-pentamethylpiperidin-4-yl)furan-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (53 mg, 0.15 mmol) was dissolved in DMF (1 mL) and HOBt (23 mg, 0.15 mmol) and EDCI (29 mg, 0.15 mmol) were added. The reaction was stirred for 1 h prior to addition of 2,2,6,6-tetramethylpiperidin-4-amine (21 mg, 0.135 mmol). The reaction was stirred for 16 h and then absorbed directly on to Isolute SCX-2 cartridge, washed with MeOH (5 mL) and then eluted with 7 N NH3 in MeOH (5 mL). The solvent was removed under a stream of N2 and the resulting crude product purified using prep method A.

Workup

  1. stirringThe reaction was stirred for 16 h
  2. customabsorbed directly on to Isolute SCX-2 cartridge
  3. washwashed with MeOH (5 mL)
  4. washeluted with 7 N NH3 in MeOH (5 mL)
  5. customThe solvent was removed under a stream of N2
  6. customthe resulting crude product purified

Sources & evidence

ORD record
ord-61460c0e247549e6b3f1e73610eb2fa4
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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