Dimethylformamide → HCID 178483813, compound

HRID 1945487Notes

Reaction equation

HRID 1945487 reaction equation
[C:1]12([C:11]3[CH:30]=[CH:29][C:14]([O:15][CH2:16][C:17]4NC5C=CC(C(O)=O)=CC=5N=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.[CH2:31]([N:33]([CH2:37]C)[CH2:34][CH2:35][NH2:36])C.CN(C(O[N:47]1N=[N:54][C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][C:48]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CN([CH:75]=[O:76])C>>[CH3:37][N:33]([CH3:31])[CH2:34][CH2:35][NH:36][C:75]([C:52]1[CH:51]=[CH:50][C:49]2[NH:54][C:17]([CH2:16][O:15][C:14]3[CH:13]=[CH:12][C:11]([C:1]45[CH2:10][CH:5]6[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]6)[CH2:2]4)[CH2:8]5)=[CH:30][CH:29]=3)=[N:47][C:48]=2[CH:53]=1)=[O:76]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 60993N,N-DiethylethylenediamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178524168HCID 178524168, compound

Product 1

HCID 178483813HCID 178483813, compoundYield 25.8%

Procedure

To solution of 2-(4-adamantan-1-yl-phenoxymethyl)-1H-benzoimidazole-5-carboxylic acid (70.0 mg, 0.18 mmol), N,N-diethylethylenediamine (23.8 mg, 0.27 mmol, 0.03 ml) and HBTU (136.5 mg, 0.36 mmol) in DMF 4.0 mL was added DIPEA (46.5 mg, 0.36 mmol, 0.06 ml). After stirring at room temperature, the mixture was partitioned between ethyl acetate and brine. The organic phase was dried (MgSO4 anh), and concentrated. The residue was purified by Prep-TLC(CH2Cl2:MeOH=10:1) to give 2-(4-adamantan-1-yl-phenoxymethyl)-1H-benzoimidazole-5-carboxylic acid (2-dimethylamino-ethyl)-amide as a yellow solid (21.9 mg, 25.8% yield).

Workup

  1. customthe mixture was partitioned between ethyl acetate and brine
  2. dry with materialThe organic phase was dried (MgSO4 anh)
  3. concentrationconcentrated
  4. customThe residue was purified by Prep-TLC(CH2Cl2:MeOH=10:1)

Sources & evidence

ORD record
ord-f6f82e3e1ada495f9f52f4c79aa6858e
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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