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

HRID 469003Notes

Reaction equation

HRID 469003 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=NC2N(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][NH2:58])=[CH:52][CH:51]=1.Cl.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[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]([NH:58][CH2:57][CH2:56][C:53]3[CH:54]=[CH:55][C:50]([C:46]4[NH:47][CH2:48][CH2:49][N:45]=4)=[CH:51][CH:52]=3)=[O:22])[CH:16]=2)[CH3:13])(=[O:10])=[O:11])=[C:4]([Cl:23])[CH:3]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 223907052-[4-(4,5-Dihydro-1H-imidazol-2-yl)phenyl]ethan-1-amineHCID 583934255-({[(4-Bromo-2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid

Product 1

HCID 461753635-({[(4-bromo-2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)-N-{2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]ethyl}furan-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

5-({[(4-bromo-2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (60 mg, 0.14 mmol)), EDCI (40 mg, 0.21 mmol) and HOAt (28 mg, 0.21 mmol) were dissolved in DMF (1 mL) and the mixture was stirred until acid activation was complete. 2-[4-(4,5-Dihydro-1H-imidazol-2-yl)phenyl]ethanamine.HCl (114 mg, 0.50 mmol) and DIPEA (0.174 mL, 1.00 mmol) were sonicated in 1 mL DMF for 5 min. The activated acid solution was added to 0.25 mL of amine solution and the reaction was stirred at ambient temperature for 3 h. The reaction was diluted with DCM (15 mL) and washed with saturated aqueous NH4Cl (2×3 mL). The organic layer was dried over MgSO4 and solvents were removed in vacuo. A portion of the crude product was purified using prep method C.

Workup

  1. stirringthe reaction was stirred at ambient temperature for 3 h
  2. washwashed with saturated aqueous NH4Cl (2×3 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

Sources & evidence

ORD record
ord-6eb4a9fea7814e52a177feed56adc814
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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