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

HRID 469002

Reaction equation

HRID 469002 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[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]([Cl:23])[CH:3]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH:45]1[CH2:49][CH2:48][N:47]=[C:46]1[C:50]1[CH:55]=[CH:54][C:53]([CH2:56][CH2:57][NH:58][CH3:59])=[CH:52][CH:51]=1.Cl.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([S:9]([N:12]([CH2:14][C:15]2[O:19][CH:18]=[C:17]([C:20]([N:58]([CH2:57][CH2:56][C:53]3[CH:52]=[CH:51][C:50]([C:46]4[NH:47][CH2:48][CH2:49][N:45]=4)=[CH:55][CH:54]=3)[CH3:59])=[O:22])[CH:16]=2)[CH3:13])(=[O:11])=[O:10])=[C:4]([Cl:23])[CH:3]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 58393425HCID 58393425, compoundHCID 672171912-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N-methylethanamine

Product 1

HCID 461753645-({[(4-bromo-2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)-N-{2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]ethyl}-N-methylfuran-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 5-({[(4-bromo-2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (54 mg, 0.12 mmol), EDCI (29 mg, 0.15 mmol) and HOBt (20 mg, 0.15 mmol) in DMF (3 mL) was added a solution of 2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N-methylethanamine.HCl (29 mg, 0.11 mmol) and DIPEA (0.084 mL, 0.48 mmol) in DMF (2 mL). The reaction was stirred at ambient temperature for 18 h, then diluted with EtOAc. The solution was washed with water, saturated aqueous NaHCO3 and 1:1 saturated brine:water. The organic extracts were dried over MgSO4, and solvent was removed in vacuo. A portion of the crude product was purified using prep method C.

Workup

  1. washThe solution was washed with water, saturated aqueous NaHCO3 and 1:1 saturated brine
  2. dry with materialThe organic extracts were dried over MgSO4, and solvent
  3. customwas removed in vacuo
  4. customA portion of the crude product was purified

Sources & evidence

ORD record
ord-868d4065189749e38d4558a0ebe7820e
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Linked notes

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