Morpholine → {3-[2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-yl]-3H-imidazole-4-yl}-morpholin-4-yl-methanone

HRID 2180004

Reaction equation

HRID 2180004 reaction equation
[CH3:1][O:2][C:3]1[C:8]([N:9]2[C:13]([C:14]([OH:16])=O)=[CH:12][N:11]=[CH:10]2)=[CH:7][C:6]([CH3:17])=[C:5]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][C:19]=2[O:29][CH3:30])[N:4]=1.[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl.O.[Na+].[Cl-]>[CH3:1][O:2][C:3]1[C:8]([N:9]2[C:13]([C:14]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[O:16])=[CH:12][N:11]=[CH:10]2)=[CH:7][C:6]([CH3:17])=[C:5]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:26])([F:27])[F:28])=[CH:20][C:19]=2[O:29][CH3:30])[N:4]=1

Participants

8

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 224900713-[2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-yl]-3H-imidazole-4-carboxylic acid

Product 1

HCID 22490048{3-[2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-yl]-3H-imidazole-4-yl}-morpholin-4-yl-methanone

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 5234Sodium ChlorideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-[2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-yl]-3H-imidazole-4-carboxylic acid (0.2 g, 0.50 mmol), morpholine (0.04 mL, 0.47 mmol) and N,N diisopropylethyl amine (0.1 mL, 0.5 mmol) in CH2Cl2 (5 mL) is treated with benzotriazol-1-yloxytris-(dimethylamino)phosphonium hexafluorophosphate (0.20 g, 0.50 mmol) and stirred at room temperature overnight. The resulting mixture is diluted with CH2Cl2 (50 mL) and water (50 mL) and saturated aqueous NaCl (50 mL). The organic portion is dried over Na2SO4, filtered and concentrated. Purification by preparative TLC (8% methanol-CH2Cl2) gives {3-[2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-yl]-3H-imidazole-4-yl}-morpholin-4-yl-methanone (Compound 6) as a white solid. TLC Rf 0.45 (elution with 8% methanol-methylene chloride).

Workup

  1. dry with materialThe organic portion is dried over Na2SO4
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customPurification by preparative TLC (8% methanol-CH2Cl2)

Sources & evidence

ORD record
ord-86111bcbd2e14e1b96fcf8abfa17e41f
Source dataset
uspto-grants-2005_05
Patent number
US06887875B2

Linked notes

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