Nitrogen → HCID 58564185, compound

HRID 555281Notes

Reaction equation

HRID 555281 reaction equation
[CH3:1][S:2]([CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]([OH:18])=O)=[CH:15][C:10]=2[N:9]=[CH:8]1)(=[O:4])=[O:3].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH2:38][CH:39]1[CH:46]2[CH2:47][C:42]3([OH:49])[CH2:43][CH:44]([CH2:48][CH:40]1[CH2:41]3)[CH2:45]2.CCN=C=NCCCN(C)C.Cl.N#N>CN(C=O)C.O>[OH:49][C:42]12[CH2:47][CH:46]3[CH2:45][CH:44]([CH2:48][CH:40]([CH:39]3[NH:38][C:16]([C:14]3[CH:13]=[CH:12][C:11]4[N:7]([CH2:6][CH2:5][S:2]([CH3:1])(=[O:3])=[O:4])[CH:8]=[N:9][C:10]=4[CH:15]=3)=[O:18])[CH2:41]1)[CH2:43]2

Participants

9

Reactant 6

HCID 947NitrogenHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 28574474-Aminoadamantan-1-olHCID 54934704HCID 54934704, compound

Product 1

HCID 58564185HCID 58564185, compoundYield 16.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(2-methanesulfonylethyl)-1H-benzoimidazole-5-carboxylic acid (0.2 g, 0.74 mmol) in DMF (5 mL) was added HOBt (0.15 g, 0.89 mmol), DIPEA (0.4 mL, 2.23 mmol), 4-aminoadamantan-1-ol (0.15 g 0.89 mmol) and EDCl (0.21 g, 1.11 mmol) successively under N2 atmosphere. The reaction mixture was allowed to stir over night at room temperature. It was diluted with water and extracted with CHCl3. The organic layer was washed with saturated NaHCO3 solution, brine and dried over anhydrous Na2SO4. Concentration of the organic layer gave 1-(2-methanesulfonylethyl)-1H-benzoimidazole-5-carboxylic acid (5-hydroxyadamantan-2-yl)-amide (0.05 g). MS-ESI m/z 418 (M+1); 1H NMR (300 MHz, CDCl3) δ 8.2 (s, 1H), 8.1 (s, 1H), 7.9 (d, 1H), 7.5 (d, 1H), 6.4 (d, 1H), 4.8 (t, 2H), 4.2 (m, 1H), 3.6 (t, 2H), 2.7 (s, 3H), 2.4 (s, 2H), 2.3 (m, 1H), 1.8 (m, 11H).

Workup

  1. extractionextracted with CHCl3
  2. washThe organic layer was washed with saturated NaHCO3 solution, brine
  3. dry with materialdried over anhydrous Na2SO4

Sources & evidence

ORD record
ord-f584534b79ca4febb854796b7c4f2ba5
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

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