1,2-Dichloroethane → HCID 24967620, compound

HRID 1945485Notes

Reaction equation

HRID 1945485 reaction equation
C12([C:11]3[CH:30]=[CH:29][C:14]([O:15][CH2:16][C:17]4[NH:21][C:20]5[CH:22]=[CH:23][C:24]([C:26]([OH:28])=O)=[CH:25][C:19]=5[N:18]=4)=[CH:13][CH:12]=3)CC3CC(CC(C3)C1)C2.[CH3:31][NH:32][CH3:33].[CH2:34](Cl)CCl.[CH:38]1[CH:39]=[CH:40][C:41]2N(O)N=N[C:42]=2[CH:43]=1.CCN([CH:54]([CH3:56])[CH3:55])C(C)C>CN(C=O)C>[CH3:31][N:32]([CH3:33])[C:26]([C:24]1[CH:23]=[CH:22][C:20]2[N:21]=[C:17]([CH2:16][O:15][C:14]3[CH:29]=[CH:30][C:11]([C:43]45[CH2:42][CH:41]6[CH2:55][CH:54]([CH2:56][CH:39]([CH2:40]6)[CH2:38]4)[CH2:34]5)=[CH:12][CH:13]=3)[NH:18][C:19]=2[CH:25]=1)=[O:28]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 674DimethylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 178524168HCID 178524168, compound

Product 1

HCID 24967620HCID 24967620, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To solution of 2-(4-adamantan-1-yl-phenoxymethyl)-1H-benzoimidazole-5-carboxylic acid (44.8 mg, 0.11 mmol), dimethyl amine (0.4 mg, 0.23 mmol), EDC (44.1 mg, 0.23 mmol) and HOBt (31.3 mg, 0.23 mmol) in DMF 4.0 mL was added DIPEA (28.8 mg, 0.23 mmol, 0.04 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-(4-adamantan-1-yl-phenoxymethyl)-3H-benzoimidazole-5-carboxylic acid dimethylamide as a yellow solid (27.8 mg, 54.0% 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 Prep-TLC (n-Hexane:EtoAc:MeOH=6:3:1)

Sources & evidence

ORD record
ord-5b31501d19bf4a7fab783d9d8e0965f3
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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