1,2-Dichloroethane → HCID 2066139, compound

HRID 1945490Notes

Reaction equation

HRID 1945490 reaction equation
ClC1C=C(Cl)C=CC=1OC[C:6]1[NH:7][C:8]2[CH:14]=[C:13]([C:15]([OH:17])=O)[CH:12]=[CH:11][C:9]=2[N:10]=1.[CH2:23]([NH2:29])[C:24]1[O:28][CH:27]=[CH:26][CH:25]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(CC1C=C(CN(C)C)C(O)=C(CN(C)C)C=1)C>[O:28]1[CH:27]=[CH:26][CH:25]=[C:24]1[CH2:23][NH:29][C:15]([C:13]1[CH:12]=[CH:11][C:9]2[N:10]=[CH:6][NH:7][C:8]=2[CH:14]=1)=[O:17]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 3438FurfurylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 24812205HCID 24812205, compound

Product 1

HCID 2066139HCID 2066139, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 70262,4,6-Tris((dimethylamino)methyl)phenolSolvent

Procedure

To solution of 2-(2,4-dichloro-phenoxymethyl)-3H-benzoimidazole-5-carboxylic acid (22.2 mg, 0.07 mmol), furfuryl amine (10.7 mg, 0.11 mmol, 0.01 ml), EDC (21.1 mg, 0.11 mmol) and HOBt (14.9 mg, 0.11 mmol) in DMF 3.0 mL was added DIPEA (14.2 mg, 0.11 mmol, 0.02 ml). After stirring at room temperature, the mixture was partitioned between ethyl acetate and 10% HCl. The organic phase was washed with brine, dried (MgSO4 anh), and concentrated. The residue was purified by Prep-TLC (n-Hexane:EtoAc:MeOH=6:3:1) to give 2-2,4-dichloro-phenoxymethyl)-3H-benzoimidazole-5-carboxylic acid (furan-2-ylmethyl)-amide as a white solid (14.7 mg, yield: 37.92%).

Workup

  1. customthe mixture was partitioned between ethyl acetate and 10% HCl
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4 anh)
  4. concentrationconcentrated
  5. customThe residue was purified by Prep-TLC (n-Hexane:EtoAc:MeOH=6:3:1)

Sources & evidence

ORD record
ord-bcedf582620b4c79873629ed4494dad2
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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