Hydrochloric Acid → N-{2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]ethyl}-5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-2-methylfuran-3-carboxamide

HRID 469029Notes

Reaction equation

HRID 469029 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][C:19]([CH3:21])=[C:18]([C:22](O)=[O:23])[CH:17]=2)[CH3:14])(=[O:12])=[O:11])=[C:5]([CH3:25])[CH:4]=1.CC[N:28]=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1.[NH:47]1[CH2:51][CH2:50][N:49]=[C:48]1[C:52]1[CH:57]=[CH:56][C:55]([CH:58](N)[CH3:59])=[CH:54][CH:53]=1.Cl.CCN(C(C)C)C(C)C>CN(C=O)C>[NH:47]1[CH2:51][CH2:50][N:49]=[C:48]1[C:52]1[CH:57]=[CH:56][C:55]([CH2:58][CH2:59][NH:28][C:22]([C:18]2[CH:17]=[C:16]([CH2:15][N:13]([S:10]([C:6]3[C:7]([CH3:9])=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[CH3:25])(=[O:12])=[O:11])[CH3:14])[O:20][C:19]=2[CH3:21])=[O:23])=[CH:54][CH:53]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 583929725-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-2-methylfuran-3-carboxylic acidHCID 672171881-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]ethanamine

Product 1

HCID 58393221N-{2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]ethyl}-5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-2-methylfuran-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-2-methylfuran-3-carboxylic acid (100 mg, 0.28 mmol) was dissolved in DMF (2 mL) and EDCI (65 mg, 0.34 mmol) and HOAt (46 mg, 0.34 mmol) were added. 1 mL of this solution was added to a flask containing 1-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]ethanamine.HCl (27 mg, 0.13 mmol) and DIPEA (0.024 mL, 0.14 mmol) in DMF (2 mL). The reaction was concentrated and diluted with DCM, then washed with saturated aqueous NH4Cl (2×2 mL) and saturated brine (2 mL), and dried over MgSO4. The filtrate was shaken with Ambersep and PL-MIA resins for 48 h, then filtered. The solvent was removed in vacuo and a portion of the crude product purified using prep method C.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with DCM
  3. washwashed with saturated aqueous NH4Cl (2×2 mL) and saturated brine (2 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo
  7. customa portion of the crude product purified

Sources & evidence

ORD record
ord-16364db9e1b64ae3afbbe361664c8134
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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