1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58393055, compound

HRID 469050Notes

Reaction equation

HRID 469050 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]([OH:23])=O)[CH:17]=2)[CH3:14])(=[O:12])=[O:11])=[C:5]([CH3:24])[CH:4]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:46][NH:47][CH2:48][C:49]1[S:50][CH:51]=[C:52]([CH2:54][N:55]2[CH2:59][CH2:58][CH2:57][CH2:56]2)[N:53]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:24])[C:6]([S:10]([N:13]([CH2:15][C:16]2[O:20][CH:19]=[C:18]([C:21]([N:47]([CH3:46])[CH2:48][C:49]3[S:50][CH:51]=[C:52]([CH2:54][N:55]4[CH2:59][CH2:58][CH2:57][CH2:56]4)[N:53]=3)=[O:23])[CH:17]=2)[CH3:14])(=[O:11])=[O:12])=[C:7]([CH3:9])[CH:8]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 583930975-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acidHCID 58393150HCID 58393150, compound

Product 1

HCID 58393055HCID 58393055, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (30 mg, 0.085 mmol) was dissolved in DCM (10 mL) and EDCI (30 mg, 0.15 mmol) and HOBt (21 mg, 0.15 mmol) were added. The resulting solution was stirred for 45 min prior to the addition of a solution of N-methyl-1-[4-(pyrrolidin-1-ylmethyl)-1,3-thiazol-2-yl]methanamine (26 mg, 0.12 mmol) in DCM (2 mL). The reaction was stirred at ambient temperature for 5 h, saturated aqueous NaHCO3 (15 mL) was added and the mixture was extracted with DCM (3×15 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo. The residue was purified by FCC eluting with 3% MeOH in DCM. A portion of the resulting product was purified by prep method B to afford the title compound.

Workup

  1. stirringThe reaction was stirred at ambient temperature for 5 h
  2. extractionthe mixture was extracted with DCM (3×15 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by FCC
  6. washeluting with 3% MeOH in DCM
  7. customA portion of the resulting product was purified by prep method B

Sources & evidence

ORD record
ord-685ab12f96f446a4ac2ef75be696416c
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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