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

HRID 469006

Reaction equation

HRID 469006 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([S:9]([N:12]([CH2:14][C:15]2[O:19][CH:18]=[C:17]([C:20]([OH:22])=O)[CH:16]=2)[CH3:13])(=[O:11])=[O:10])=[C:4]([CH3:23])[CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH:36]1[CH2:40][CH2:39][N:38]=[C:37]1[C:41]1[CH:46]=[CH:45][C:44]([CH2:47][CH2:48][NH:49][CH3:50])=[CH:43][CH:42]=1.Cl.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([S:9]([N:12]([CH2:14][C:15]2[O:19][CH:18]=[C:17]([C:20]([N:49]([CH2:48][CH2:47][C:44]3[CH:43]=[CH:42][C:41]([C:37]4[NH:38][CH2:39][CH2:40][N:36]=4)=[CH:46][CH:45]=3)[CH3:50])=[O:22])[CH:16]=2)[CH3:13])(=[O:11])=[O:10])=[C:4]([CH3:23])[CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 583930295-({[(4-Chloro-2,5-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acidHCID 672171912-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N-methylethanamine

Product 1

HCID 583930965-({[(4-chloro-2,5-dimethylphenyl)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 6228DimethylformamideSolvent2×

Procedure

5-({[(4-chloro-2,5-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (30 mg, 0.08 mmol) was dissolved in DMF (1 mL) and CDI (20 mg, 0.12 mmol) was added. The mixture was stirred until acid activation was complete. 2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N-methylethanamine.HCl (19 mg, 0.08 mmol) and DIPEA (0.042 mL, 0.24 mmol) were sonicated in DMF (1 mL) for 15 min, 0.5 mL of activated acid solution was added to 0.25 mL of amine solution and the reaction was microwaved (120° C., 200 W) for 20 min, then 2×60 min. A portion of the reaction was concentrated and purified using prep method A.

Workup

  1. customthe reaction was microwaved (120° C., 200 W) for 20 min
  2. custom2×60 min
  3. concentrationA portion of the reaction was concentrated
  4. custompurified

Sources & evidence

ORD record
ord-4d14727ff2774839ac87213170d252f8
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Linked notes

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