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

HRID 468997Notes

Reaction equation

HRID 468997 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][NH:57][CH3:58])=[CH:52][CH:51]=1.Cl.CCN(C(C)C)C(C)C>CN(C=O)C>[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: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)[CH3:58])=[O:22])[CH:16]=2)[CH3:13])(=[O:10])=[O:11])=[C:4]([Cl:23])[CH:3]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 552648631-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N-methylmethanamineHCID 583934255-({[(4-Bromo-2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid

Product 1

HCID 461754535-({[(4-bromo-2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)-N-[4-(4,5-dihydro-1H-imidazol-2-yl)benzyl]-N-methylfuran-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 5-({[(4-bromo-2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (60 mg, 0.14 mmol), EDCI (33 mg, 0.17 mmol) and HOAt (23 mg, 0.17 mmol) in DMF (0.5 mL) was added a solution of 1-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N-methylmethanamine.HCl (28 mg, 0.13 mmol) and DIPEA (0.025 mL, 0.14 mmol) in DMF (0.5 mL). The reaction was heated to 60° C. for 5 h, then concentrated and diluted with DCM. The solution was washed with saturated aqueous NH4Cl(2×2 mL) and saturated brine (2 mL), and dried over MgSO4. The filtrate was shaken with Ambersep resin for 48 h, then filtered. The solvent was removed in vacuo and a portion of the crude product purified using prep method C.

Workup

  1. concentrationconcentrated
  2. additiondiluted with DCM
  3. washThe solution was washed with saturated aqueous NH4Cl(2×2 mL) and saturated brine (2 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo
  7. customa portion of the crude product purified

Sources & evidence

ORD record
ord-5d9a0c45104c4bbd97dc98b1ad388ce9
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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