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

HRID 469000Notes

Reaction equation

HRID 469000 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([N:12]([CH2:14][C:15]1[O:19][CH:18]=[C:17]([C:20](O)=[O:21])[CH:16]=1)[CH3:13])(=[O:11])=[O:10].C1N=CN(C(N2C=NC=C2)=O)C=1.[NH:35]1[CH2:39][CH2:38][N:37]=[C:36]1[C:40]1[CH:45]=[CH:44][C:43]([CH2:46][CH2:47][NH:48][CH3:49])=[CH:42][CH:41]=1.Cl>ClCCCl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([N:12]([CH2:14][C:15]1[O:19][CH:18]=[C:17]([C:20]([N:48]([CH2:47][CH2:46][C:43]2[CH:42]=[CH:41][C:40]([C:36]3[NH:37][CH2:38][CH2:39][N:35]=3)=[CH:45][CH:44]=2)[CH3:49])=[O:21])[CH:16]=1)[CH3:13])(=[O:10])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 583932675-({[(2,4-Dichlorophenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acidHCID 672171912-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N-methylethanamine

Product 1

HCID 461753665-({[(2,4-dichlorophenyl)sulfonyl](methyl)amino}methyl)-N-{2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]ethyl}-N-methylfuran-3-carboxamide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

5-({[(2,4-dichlorophenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (34 mg, 0.08 mmol) was dissolved in DCE (1 mL) and CDI (26 mg, 0.16 mmol) was added. The reaction was stirred for 2 h. The activated acid solution in DCE was added to a vial containing 2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N-methylethanamine.HCl (43 mg, 0.16 mmol) and TEA (0.022 mL, 0.16 mmol). The reaction was stirred at ambient temperature for 18 h, then partitioned between saturated aqueous NaHCO3 (1 mL) and DCE (3×1 mL)). The organic layer was dried over MgSO4 and solvents were removed in vacuo. A portion of the crude product was purified by prep method A.

Workup

  1. stirringThe reaction was stirred at ambient temperature for 18 h
  2. custompartitioned between saturated aqueous NaHCO3 (1 mL) and DCE (3×1 mL))
  3. dry with materialThe organic layer was dried over MgSO4 and solvents
  4. customwere removed in vacuo
  5. customA portion of the crude product was purified by prep method A

Sources & evidence

ORD record
ord-f0da3c52aec746758d726e76ec0b00ab
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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