Water → HCID 178523026, compound

HRID 1945486Notes

Reaction equation

HRID 1945486 reaction equation
[C:1]12([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)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH2:31]([NH2:37])[C:32]1[O:36][CH:35]=[CH:34][CH:33]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.O>CN(C1C=CN=CC=1)C.CN(C=O)C>[O:36]1[CH:35]=[CH:34][CH:33]=[C:32]1[CH2:31][NH:37][C:26]([C:24]1[CH:23]=[CH:22][C:20]2[NH:21][C:17]([CH2:16][O:15][C:14]3[CH:29]=[CH:30][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:12][CH:13]=3)=[N:18][C:19]=2[CH:25]=1)=[O:28]

Participants

7

Reactant 4

HCID 962WaterHCID 3438FurfurylamineHCID 2724699PyBOPHCID 178524168HCID 178524168, compound

Product 1

HCID 178523026HCID 178523026, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-adamantan-1-yl-phenoxymethyl)-1H-benzoimidazole-5-carboxylic acid (50 mg, 0.124 mmol), furfuryl amine (18 mg, 0.186 mmol) and DMAP (22.78 mg, 0.186 mmol) in DMF (1 mL) was added PyBOP (97 mg, 0.186 mmol) at room temperature. The mixture was stirred for 16 h at room temperature and then poured into water (150 mL). The resulting solid was extracted with a mixture of methanol:MC (10%), washed with brine, aqueous sodium bicarbonate and water, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The resulted crude product was purified by PLC (methanol: MC=0.5:9.5) to afford 2-(4-adamantan-1-yl-phenoxymethyl)-1H-benzoimidazole-5-carboxylic acid (furan-2-ylmethyl)-amide as a colorless solid (43.2 mg, 72% yield).

Workup

  1. extractionThe resulting solid was extracted with a mixture of methanol
  2. washMC (10%), washed with brine, aqueous sodium bicarbonate and water
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulted crude product
  7. customwas purified by PLC (methanol: MC=0.5:9.5)

Sources & evidence

ORD record
ord-bf8a8077eff3438a9cb5b4d5715294c6
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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