Dicyclohexylcarbodiimide → N-(2-morpholinyl-ethyl)-5-[4,5-bis(4-methoxyphenyl)-1H-imidazol-2-ylthio]-pentanamide

HRID 1708390Notes

Reaction equation

HRID 1708390 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([S:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=O)[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.O.ON1C2C=CC=CC=2N=N1.[NH2:41][CH2:42][CH2:43][N:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1.C(OCC)(=O)C>[N:44]1([CH2:43][CH2:42][NH:41][C:27](=[O:29])[CH2:26][CH2:25][CH2:24][CH2:23][S:22][C:11]2[NH:10][C:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)=[C:13]([C:14]3[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[N:12]=2)[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 4082852-MorpholinoethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 100473085-[4,5-bis(4-methoxyphenyl)-1H-imidazol-2-ylthio]pentanoic acid

Product 1

HCID 10052537N-(2-morpholinyl-ethyl)-5-[4,5-bis(4-methoxyphenyl)-1H-imidazol-2-ylthio]-pentanamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-[4,5-bis(4-methoxyphenyl)-1H-imidazol-2-ylthio]pentanoic acid (1.91 g, 4.63 mmol) and 1-hydroxy-1H-benzotriazole hydrate (890 rag, 6.59 mmol) in tetrahydrofuran (20 mL) was cooled to 0° C., and treated with 2-aminoethylmorpholine (1.0 mL, 7.62 mmol). After 20 minutes, dicyclohexylcarbodiimide (1.42 g, 6.88 mmol) was added in small portions over 20 minutes. This mixture was allowed to stir an additional 48 hours, then poured into ethyl acetate (250 mL), filtered, and washed with water (200 mL). The phases were separated, and the aqueous phase was saturated with sodium chloride and reextracted with methylene chloride (200 mL). The organic phases were combined, dried over anhydrous sodium sulfate and evaporated. The mixture was separated by flash chromatography to afford the product, N-(2-morpholinyl-ethyl)-5-[4,5-bis(4-methoxyphenyl)-1H-imidazol-2-ylthio]-pentanamide, as an oil (1.77 g, 3.37 mmol, 73%). 1H NMR (CDCl3): 7.42 (4H, br d, J=9 Hz); 6.82 (4H, d, J=9 Hz); 6.22 (1H, br t, J=4 Hz); 3.80 (6H, s); 3.65-3.60 (4H, m); 3.15 (2H, q, J=6 Hz); 2.98 (2H, t, J=7 Hz); 2.38-2.24 (8H, m); 1.96-1.85 (2H, m); 1.70-1.60 (2H, m).

Workup

  1. filtrationfiltered
  2. washwashed with water (200 mL)
  3. customThe phases were separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe mixture was separated by flash chromatography

Sources & evidence

ORD record
ord-d6eaf97ce31548bd875d62dfb38cf9ea
Source dataset
uspto-grants-1994_10
Patent number
US05358946

Reaction notes

Loading…