1,2-Dichloroethane → HCID 24812206, compound

HRID 1945484Notes

Reaction equation

HRID 1945484 reaction equation
[C:1]12([C:11]3[CH:30]=[CH:29][C:14]([O:15][CH2:16][C:17]4[NH:18][C:19]5[CH:25]=[C:24]([C:26](O)=[O:27])[CH:23]=[CH:22][C:20]=5[N:21]=4)=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[Cl-].[NH4+].C(Cl)CCl.C1C=CC2N(O)N=[N:43]C=2C=1.CCN(C(C)C)C(C)C>CN(CC1C=C(CN(C)C)C(O)=C(CN(C)C)C=1)C>[C:1]12([C:11]3[CH:30]=[CH:29][C:14]([O:15][CH2:16][C:17]4[NH:18][C:19]5[CH:25]=[C:24]([C:26]([NH2:43])=[O:27])[CH:23]=[CH:22][C:20]=5[N:21]=4)=[CH:13][CH:12]=3)[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 24966536HCID 24966536, compound

Product 1

HCID 24812206HCID 24812206, compoundYield 38%

Reagents, catalysts & solvents 1

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

Procedure

To solution of 2-(4-adamantan-1-yl-phenoxymethyl)-3H-benzoimidazole-5-carboxylic acid (44-0.8 mg, 0.11 mmol), ammonium chloride (11.8 mg, 0.22 mmol), EDC (32.6 mg, 0.17 mmol) and HOBt (23.0 mg, 0.17 mmol) in DMF 3.0 mL was added DIPEA (0.03 ml 0.17 mmol). 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 silica gel column chromatography (CH2Cl2:MeOH=6:1) to give 2-(4-adamantan-1-yl phenoxymethyl)-3H benzoimidazole-5-carboxylic acid amide as a white solid (16.8 mg, 37.5% yield).

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 silica gel column chromatography (CH2Cl2:MeOH=6:1)

Sources & evidence

ORD record
ord-b64c8693f29744c39644c66badf8b065
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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