Hydrochloric Acid → 5-({[(2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)-N-[4-(4,5-dihydro-1H-imidazol-2-yl)benzyl]furan-3-carboxamide

HRID 469004Notes

Reaction equation

HRID 469004 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[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][NH2:47])=[CH:42][CH:41]=1.Cl.CCN(C(C)C)C(C)C>ClCCCl.CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[S:9]([N:12]([CH2:14][C:15]1[O:19][CH:18]=[C:17]([C:20]([NH: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)=[O:21])[CH:16]=1)[CH3:13])(=[O:11])=[O:10]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 552648641-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methanamineHCID 583932575-({[(2,6-Dichlorophenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid

Product 1

HCID 461753625-({[(2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)-N-[4-(4,5-dihydro-1H-imidazol-2-yl)benzyl]furan-3-carboxamide

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent2×

Procedure

5-({[(2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (51 mg, 0.14 mmol) was dissolved in DCE (0.5 mL) and CDI (34 mg, 0.21 mmol) was added. The mixture was stirred until acid activation was complete. 1-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methanamine.HCl (180 mg, 0.42 mmol) and DIPEA (0.22 mL, 1.26 mmol) were sonicated in DMF (3 mL) for 15 min, 0.25 mL of activated acid solution was added to 0.5 mL of amine solution and the reaction was diluted with DMF (1.5 mL) and stirred at ambient temperature for 18 h. The reaction was concentrated, dissolved in DCM and washed with water (3×1.5 mL) and saturated brine (1 mL)). The organic layer was dried over MgSO4, shaken with Ambersep and PL-MIA resins, and solvents were removed in vacuo. A portion of the crude product was purified using prep method C.

Workup

  1. stirringstirred at ambient temperature for 18 h
  2. concentrationThe reaction was concentrated
  3. dissolutiondissolved in DCM
  4. washwashed with water (3×1.5 mL) and saturated brine (1 mL))
  5. dry with materialThe organic layer was dried over MgSO4
  6. stirringshaken with Ambersep and PL-MIA resins, and solvents
  7. customwere removed in vacuo
  8. customA portion of the crude product was purified

Sources & evidence

ORD record
ord-01ee525b6fd045f59d1b681dd79cf32d
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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