Diisopropylethylamine → N-(3 hydroxyadamant-1-yl)-2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxamide

HRID 1428991Notes

Reaction equation

HRID 1428991 reaction equation
[CH3:1][C:2]1[N:3]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:4]([CH3:10])=[C:5]([C:7]([OH:9])=O)[N:6]=1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.ClC1N(C)CC[NH+]1C.[OH:41][C:42]12[CH2:51][CH:46]3[CH2:47][CH:48]([CH2:50][C:44]([NH2:52])([CH2:45]3)[CH2:43]1)[CH2:49]2>ClCCl>[OH:41][C:42]12[CH2:51][CH:46]3[CH2:47][CH:48]([CH2:50][C:44]([NH:52][C:7]([C:5]4[N:6]=[C:2]([CH3:1])[N:3]([C:11]5[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=5)[C:4]=4[CH3:10])=[O:9])([CH2:45]3)[CH2:43]1)[CH2:49]2

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 6586453-Amino-1-adamantanolHCID 218684192-Chloro-1,3-dimethylimidazolidin-1-ium;hexafluorophosphateHCID 545792222,5-dimethyl-1-phenyl-1H-imidazole-4-carboxylic acid

Product 1

HCID 58695776N-(3 hydroxyadamant-1-yl)-2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxamideYield 67.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a magnetically stirred solution of 2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxylic acid (0.66 gram, 0.00306 mol) in dichloromethane (35 ml) was successively added diisopropylethylamine (DIPEA) (3.1 ml), CIP (2-chloro-1,3-dimethylimidazolinium hexafluorophosphate). (2.55 gram) and 3-hydroxyadamantane amine (0.612 gram, 0.00366 mol). The resulting mixture was reacted at 20° C. for 16 hours and subsequently concentrated in vacuo. The resulting residue was taken up in dichloromethane and washed with 5% aqueous NaHCO3 solution. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The resulting residue was purified by flash chromatography (dichoromethane/methanol=98/2 (v/v)) to give N-(3 hydroxyadamant-1-yl)-2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxamide (0.75 gram, 67% yield). Rf (silica gel/dichoromethane/methanol=98/2 (v/v))˜0.6. Melting point: 215-220° C.

Workup

  1. customThe resulting mixture was reacted at 20° C. for 16 hours
  2. concentrationsubsequently concentrated in vacuo
  3. washwashed with 5% aqueous NaHCO3 solution
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by flash chromatography (dichoromethane/methanol=98/2 (v/v))

Sources & evidence

ORD record
ord-1393384b68b146fdafa96a648774b271
Source dataset
uspto-grants-2015_01
Patent number
US08937184B2

Reaction notes

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